- Amberlyst 15 as a mild and effective activator for the glycosylation with disarmed glycosyl trichloroacetimidate donors
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Amberlyst 15 acidic resin has been shown to be a mild and effective activator for the glycosylation with commonly used disarmed glycosyl trichloroacetimidate donors. Glucosylation, galactosylation, rhamnosylation, and lactosylation of a panel of representative alcohol and thiol acceptors promoted by Amberlyst 15 allowed for the formation of structurally diverse O- or S-linked oligosaccharides and glycosylated amino acids in moderate to excellent yields.
- Tian, Qiang,Zhang, Shuo,Yu, Qian,He, Mei-Bo,Yang, Jin-Song
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Read Online
- Isolation of a Glucosidic β-Damascenone Precursor from Rose Petals
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The 9-O-β-D-glucopyranoside of 3-hydroxy-7,8-didehydro-β-ionol (1) has been isolated from a glycosidic XAD-2 extract obtained from rose petals. In addition to the β-damascenone-generating compound 1, the following glycoconjugates have been isolated and characterized as peracetates: 3-hydroxy-7,8-dihydro-β-ionol 9-O-β-D-glucopyranoside (2), 3-hydroxy-7,8-dihydro-β-ionol 3-O-β-D-glucopyranoside (3), 2-phenylethyl-O-β-D-glucopyranoside (4), 2-phenylethyl-O-β-D-galactopyranoside (5), benzyl-O-β-D-glucopyranoside (6), (2E)-2,6-dimethyl-6-hydroxyocta-2,7-dienyl-O-β-D-glucopyranoside (7), (2Z)-2,6-dimethyl-6-hydroxyocta-2,7-dienyl-O-β-D-glucopyranoside (8), and (2E,6E)-2,6-dimethyl-1-hydroxyocta-2,6-dien-8-yl-O-β-D-glucopyranoside (9).
- Straubinger, Markus,Knapp, Holger,Oka, Noriaki,Watanabe, Naoharu,Winterhalter, Peter
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- Synthesis of glycosides via indium(III) chloride mediated activation of glycosyl halide in neutral condition
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Various glycosides and disaccharides were synthesized through coupling of glycosyl bromides with acceptors in presence of indium chloride as a promoter. Glycosidation reactions proceeded with high stereoselectivity.
- Mukherjee, Debaraj,Kumar Ray, Pradip,Sankar Chowdhury, Uday
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Read Online
- Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates
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Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har
- Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.
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Read Online
- PHENOLIC PLANT GROWTH INHIBITORS FROM THE FLOWERS OF CUCURBITA PEPO
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Eleven compounds isolated from the growth inhibiting active fraction of male flowers of Cucurbita pepo, were identified as p-hydroxybenzaldehyde, anisyl alcohol, p-hydroxybenzyl methyl ether, p-hydroxybenzyl alcohol, veratryl alcohol, isovanillyl alcohol, p-coumaric acid, phloretic acid, benzyl-β-D-glucoside, 4-methoxybenzyl-β-D-glucoside ans 3,4-dimethoxybenzyl-β-D-glucoside.Each compound was assayed for growth inhibiting activity using lettuce seedlings; three showed strong activity, whereas the glucosides were inactive.Key Word Index - Cucurbita pepo; Cucurbitaceae; male flowers; plant growth inhibitor; benzyl glucoside; 4-methoxybenzyl glucoside; 3,4-methoxybenzyl glucoside.
- Itokawa, Hideji,Oshida, Yoshiaki,Ikuta, Akira,Inatomi, Hideo,Adachi, Takashi
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- Chavicol β-D-glucoside, a phenylpropanoid heteroside, benzyl-β-D-glucoside and glycosidically bound volatiles from subspecies of Cedronella canariensis
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The volatile substances obtained after enzymatic hydrolysis of purified polar extracts from the aerial parts of two subspecies of Cedronella canariensis were shown to be, among others, benzyl alcohol (29.4percent), chavicol (11.6percent), cis-3-hexenol (9.3percent), 2-phenylethanol (8.6percent), cis-pinocarveol (5.1percent), myrtenol (2.2percent), 1-phenylethanol (2.0percent, tentatively), 1-octen-3-ol (1.8percent), 1-hexanol (1.1percent) for ssp. canariensis and chavicol (85.1percent), benzyl alcohol (2.5percent), cis-3-hexenol (2.5percent), 1-octen-3-ol (2.3percent); 1-hexanol (0.8percent) for ssp. anisata.Sugars detected in the polar fraction after hydrolysis were glucose, rhamnose and fructose.The main glycosides obtained from the polar fraction before hydrolysis were chavicol glucoside (6 ppm, ssp. anisata) and benzyl alcohol glucoside (2 ppm, ssp. canariensis).
- Coen, Matthias,Engel, Ralf,Nahrstedt, Adolf
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- Glycosylation in ionic liquids
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Glycosyl trichloroacetimidates react smoothly in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst with a variety of alcohols and monosaccharides in [bmim]PF6 (1-butyl-3-methylimidazolium hexafluorophosphate) as a solvent to afford the corresponding glycosides or disaccharides.
- Pakulski, Zbigniew
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Read Online
- Organocatalysis Linked to Charge-Enhanced Acidity with Superelectrophilic Traits
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Hydrogen bonding is ubiquitous throughout nature and serves as a versatile platform for accessing chemical reactivity. In leveraging this force, chemists have utilized organocatalysts to expand the spectrum of chemical reactivity enabled by hydrogen bondi
- Smajlagic, Ivor,White, Brandon,Azeez, Oyindamola,Pilkington, Melanie,Dudding, Travis
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p. 1128 - 1138
(2022/01/19)
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- Rhamnogalacturonan II: Chemical Synthesis of a Substructure Including α-2,3-Linked Kdo**
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The synthesis of a fully deprotected Kdo-containing rhamnogalacturonan II pentasaccharide is described. The strategy relies on the preparation of a suitably protected homogalacturonan tetrasaccharide backbone, through a post-glycosylation oxidation approach, and its stereoselective glycosylation with a Kdo fluoride donor.
- Mancuso, Enzo,Romanò, Cecilia,Trattnig, Nino,Gritsch, Philipp,Kosma, Paul,Clausen, Mads H.
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supporting information
p. 7099 - 7102
(2021/04/19)
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- INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF
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Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the i
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Paragraph 00513
(2021/08/14)
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- Tea leaf perfumery precursor glucoside and synthesizing method thereof
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The invention relates to a tea leaf perfumery precursor glucoside and a synthesizing method thereof. The synthesizing method comprises the following steps of synthesizing ten glucosides including aromatic alcohol ( alkanol )-beta -D-glucosides and aromatic alcohol (alkanol )-beta -D-primrose indicans. The synthesizing method disclosed by the invention is a glucoside synthesizing method which is good in selectivity, high in production rate and low in cost.
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- Conformationally Controlled Reactivity of Carbasugars Uncovers the Choreography of Glycoside Hydrolase Catalysis
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Glycoside hydrolases (GHs) catalyze hydrolyses of glycoconjugates in which the enzyme choreographs a series of conformational changes during the catalytic cycle. As a result, some GH families, including α-amylases (GH13), have their chemical steps conceal
- Adabala, Pal John Pal,Akintola, Oluwafemi,Bennet, Andrew J.,Bhosale, Sandeep,Shamsi Kazem Abadi, Saeideh
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p. 3336 - 3348
(2020/03/23)
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- A method for one-step synthesis of peracetylated-alpha-O-benzyl saccharides
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The invention relates to the technical field of chemical synthetic methods of saccharides, and particularly relates to a method for one-step synthesis of peracetylated-alpha-O-benzyl saccharides. A peracetylated monosaccharide is adopted as a donor, benzyl alcohol is adopted as a receptor, 1,2-dichloroethane is adopted as a reaction solvent, a peracetylated-alpha-O-benzyl saccharide is synthesizedthrough reaction under catalysis of ferric chloride anhydrous, and the reaction temperature is 10-40 DEG C. The method is high in regional universality, low in receptor consumption, mild in reactionconditions, high in yield, and high in stereoselectivity and can be used for large-scale production of target products. The catalyst is nontoxic and easily available.
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Paragraph 0053-0055; 0058; 0074-0075; 0083-0084
(2018/12/02)
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- Metal-free and VOC-free: O -glycosylation in supercritical CO2
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Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylation reactions in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology described here can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, with glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and are shown to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.
- Cardona, Adrià,Boutureira, Omar,Castillón, Sergio,Díaz, Yolanda,Matheu, M. Isabel
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p. 2687 - 2694
(2017/07/17)
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- AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature
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Activation of sulfoxide as glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20–60 min), facile at room temperature and the reactions conditions tolerate acid sensitive groups.
- Palanivel, Ashokkumar,Chennaiah, Ande,Dubbu, Sateesh,Mallick, Asadulla,Vankar, Yashwant D.
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- Phosphoryl mannopentaose and derivatives thereof, and preparation methods and application thereof
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The invention provides phosphoryl mannopentaose as shown in a formula (I) and derivatives as shown in formula (II) to (XI) of phosphoryl mannopentaose, and preparation methods thereof. According to the preparation methods, reactivity is regulated and cont
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Paragraph 0150; 0151
(2017/06/02)
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- Ceric ammonium nitrate/acetic anhydride: A tunable system for the O-acetylation and mononitration of diversely protected carbohydrates
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Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the es
- Seepersaud, Mohindra,Seecharan, Savita,Lalgee, Lorale J.,Jalsa, Nigel Kevin
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supporting information
p. 853 - 871
(2017/04/27)
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- A versatile glycosylation strategy: Via Au(III) catalyzed activation of thioglycoside donors
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Among various methods of chemical glycosylations, glycosylation by activation of thioglycoside donors using a thiophilic promoter is an important strategy. Many promoters have been developed for the activation of thioglycosides. However, incompatibility w
- Vibhute, Amol M.,Dhaka, Arun,Athiyarath, Vignesh,Sureshan, Kana M.
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p. 4259 - 4263
(2016/07/06)
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- Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo
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Glycoconjugation is a promising strategy for specific targeting of cancer. In this study, we investigated the effect of d-glucose substitution position on the biological activity of glucose-platinum conjugates (Glc-Pts). We synthesized and characterized all possible positional isomers (C1α, C1β, C2, C3, C4, and C6) of a Glc-Pt. The synthetic routes presented here could, in principle, be extended to prepare glucose conjugates with different active ingredients, other than platinum. The biological activities of the compounds were evaluated both in vitro and in vivo. We discovered that varying the position of substitution of d-glucose alters not only the cellular uptake and cytotoxicity profile but also the GLUT1 specificity of resulting glycoconjugates, where GLUT1 is glucose transporter 1. The C1α- and C2-substituted Glc-Pts (1α and 2) accumulate in cancer cells most efficiently compared to the others, whereas the C3-Glc-Pt (3) is taken up least efficiently. Compounds 1α and 2 are more potent compared to 3 in DU145 cells. The α- and β-anomers of the C1-Glc-Pt also differ significantly in their cellular uptake and activity profiles. No significant differences in uptake of the Glc-Pts were observed in non-cancerous RWPE2 cells. The GLUT1 specificity of the Glc-Pts was evaluated by determining the cellular uptake in the absence and in the presence of the GLUT1 inhibitor cytochalasin B, and by comparing their anticancer activity in DU145 cells and a GLUT1 knockdown cell line. The results reveal that C2-substituted Glc-Pt 2 has the highest GLUT1-specific internalization, which also reflects the best cancer-targeting ability. In a syngeneic breast cancer mouse model overexpressing GLUT1, compound 2 showed antitumor efficacy and selective uptake in tumors with no observable toxicity. This study thus reveals the synthesis of all positional isomers of d-glucose substitution for platinum warheads with detailed glycotargeting characterization in cancer.
- Patra, Malay,Awuah, Samuel G.,Lippard, Stephen J.
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supporting information
p. 12541 - 12551
(2016/10/07)
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- AuCl3- and AuCl3-Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates
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Glycosylations of armed and disarmed trichloroacetimidate-based glycosyl donors were carried out by using the AuCl3-phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5-45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature. We have reported a convenient room temperature protocol that employs AuCl3 and phenylacetylene as a catalyst system to carry out the glycosylation of glycosyl trichloroacetimidates. The effectiveness of this relay catalyst system was also compared with that of using AuCl3 alone to catalyze the glycosylations.
- Roy, Rashmi,Palanivel, Ashok Kumar,Mallick, Asadulla,Vankar, Yashwant D.
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p. 4000 - 4005
(2015/06/30)
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- Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger
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A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-β-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
- Gu, Xiangying,Chen, Lin,Wang, Xin,Liu, Xiao,You, Qidong,Xi, Wenwei,Gao, Li,Chen, Guohua,Chen, Yue-Lei,Xiong, Bing,Shen, Jingkang
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p. 1100 - 1110
(2014/03/21)
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- 1,2-cis Alkyl glycosides: Straightforward glycosylation from unprotected 1-thioglycosyl donors
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A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.
- Meng, Bo,Zhu, Zhenqian,Baker, David C.
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p. 5182 - 5191
(2014/07/08)
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- "One-pot" access to α-d-mannopyranosides from glycals employing ruthenium catalysis
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Ru-catalyzed synthesis of α-d-mannopyranosides from glucal is described via one-pot glycosylation-dihydroxylation reaction. This method is amenable to a variety of acceptors, including carbohydrate-derived and amino-acid containing alcohols to obtain mannosylated peptides and disaccharides.
- Chittela, Sravanthi,Reddy, Thurpu Raghavender,Krishna, Palakodety Radha,Kashyap, Sudhir
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p. 46327 - 46331
(2015/02/19)
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- Strained olefin enables triflic anhydride mediated direct dehydrative glycosylation
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For the first time, we demonstrated that Tf2O mediated direct dehydrative glycosylation was possible simply with strained olefins, and other typical bases were inhibitors of this reaction. We optimized the glycosylation conditions and found tha
- Chen, Guohua,Yin, Qiang,Yin, Jian,Gu, Xiangying,Liu, Xiao,You, Qidong,Chen, Yue-Lei,Xiong, Bing,Shen, Jingkang
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supporting information
p. 9781 - 9785
(2015/01/08)
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- TANNIN INHIBITORS OF HIV
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The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.
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Paragraph 0027
(2013/10/07)
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- Solvent-free mechanochemical glycosylation in ball mill
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Starting from acetobromosugars and an alcohol (alkyl/substituted alkyl/akenyl/alkynyl/glyceryl/cyclohexyl/steryl) various O-glycosides have been prepared mechanochemically under solvent-free conditions employing a planetary ball mill in the presence of metal carbonates (environmentally benign or otherwise) as promoters. The method was proven to be mild and efficient and applicable on preparative scale for the synthesis of various mono- and disaccharide glycosides. 4-Pentenyl glycoside so produced could, in four successive reactions in the same pot, be converted in high isolated yields into triazole-substituted pentyl glycoside that can find application in the area of medicinal chemistry.
- Tyagi, Mohit,Khurana, Darpan,Ravindranathan Kartha
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- Chondroitin-4-O-sulfatase from Bacteroides thetaiotaomicron: Exploration of the substrate specificity
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Bacterial sulfatases can be good tools to increase the molecular diversity of glycosaminoglycan synthetic fragments. A chondroitin 4-O-sulfatase from the human commensal bacterium Bacteroides thetaiotaomicron has recently been identified and expressed. In order to use this enzyme for synthetic purposes, the minimal structure required for its activity has been determined. For that, four 4-O-sulfated monosaccharides and one 4-O-sulfated disaccharide have been synthesized and used as substrates with the sulfatase. The minimum structure was shown to be a disaccharide but in contrast to the natural substrate, which must have a 4,5-insaturation, the enzyme accepts as substrate, a disaccharide with a saturated glucuronic acid at the non-reducing end and even a glucopyranosyl moiety without the carboxylic acid functionality.
- Malleron, Annie,Benjdia, Alhosna,Berteau, Olivier,Le Narvor, Christine
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scheme or table
p. 96 - 99
(2012/07/01)
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- Using In(III) as a promoter for glycosylation
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InCl3, InBr3, and In(OTf)3 were tested as promoters in the preparation of glycosides from trichloroacetimidate precursors. A range of protecting groups and of alcohol acceptors were used to determine the versatility of these promoters. Disaccharide formation was demonstrated. In most cases, the In(III) compounds were shown to promote glycosylation better than the widely used promoter BF3·OEt2.
- Mattson, Amanda L.,Michel, Anna K.,Cloninger, Mary J.
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scheme or table
p. 142 - 146
(2012/03/10)
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- Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity
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A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cel
- Zheng, Shaojun,Laraia, Luca,O'Connor, Cornelius J.,Sorrell, David,Tan, Yaw Sing,Xu, Zhaochao,Venkitaraman, Ashok R.,Wu, Wenjun,Spring, David R.
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supporting information; experimental part
p. 2590 - 2593
(2012/04/23)
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- Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst
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Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield.
- Guchhait, Goutam,Misra, Anup Kumar
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experimental part
p. 52 - 57
(2012/01/15)
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- Photoionization mass spectrometry: A useful method to evaluate the pyrolysis process of glycoside flavor precursor
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The thermal decomposition behavior and the pyrolysis products of benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (BGLU) were studied with synchrotron vacuum ultraviolet (VUV) photoionization mass spectrometry at temperatures of 300, 500 and 700 °C at 0.062 Pa. Several pyrolysis products and intermediates were identified by the measurement of photoionization mass spectra at different photon energies. The results indicated that the primary decomposition reaction was the cleavage of O-glycosidic bond of the glycoside at low temperature, proven by the discoveries of benzyloxy radical (m/z = 107) and glycon radical (m/z = 331) in mass spectra. As pyrolysis temperature increased from 300 to 700 °C, two possible pyrolytic modes were observed. This work reported an application of synchrotron VUV photoionization mass spectrometry in the study of the thermal decomposition of glycoside flavor precursor, which was expected to help understand the thermal decomposition mechanism of this type of compound. The possibility of this glycoside to be used as a flavor precursor in high temperature process was evaluated.
- Ding, Yu,Cai, Ji-Bao,Qi, Fei,Su, Qing-De
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p. 290 - 295
(2011/10/13)
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- First and biomimetic total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A
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The first total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A, was accomplished by relying on a biomimetic aldol-type formation of its characteristic C-aryl glucosidic bond through the exploitation of the inherent chemical reactivity of a glucopyranosic hemiacetal precursor.
- Deffieux, Denis,Natangelo, Anna,Malik, Gaelle,Pouysegu, Laurent,Charris, Jaime,Quideau, Stephane
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supporting information; experimental part
p. 1628 - 1630
(2011/03/22)
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- Structure-based drug design and optimization of mannoside bacterial fimH antagonists
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FimH-mediated cellular adhesion to mannosylated proteins is critical in the ability of uropathogenic E. coli (UPEC) to colonize and invade the bladder epithelium during urinary tract infection. We describe the discovery and optimization of potent small-molecule FimH bacterial adhesion antagonists based on α-d-mannose 1-position anomeric glycosides using X-ray structure-guided drug design. Optimized biarylmannosides display low nanomolar binding affinity for FimH in a fluorescence polarization assay and submicromolar cellular activity in a hemagglutination (HA) functional cell assay of bacterial adhesion. X-ray crystallography demonstrates that the biphenyl moiety makes several key interactions with the outer surface of FimH including π-π interactions with Tyr-48 and an H-bonding electrostatic interaction with the Arg-98/Glu-50 salt bridge. Dimeric analogues linked through the biaryl ring show an impressive 8-fold increase in potency relative to monomeric matched pairs and represent the most potent FimH antagonists identified to date. The FimH antagonists described herein hold great potential for development as novel therapeutics for the effective treatment of urinary tract infections.
- Han, Zhenfu,Pinkner, Jerome S.,Ford, Bradley,Obermann, Robert,Nolan, William,Wildman, Scott A.,Hobbs, Doug,Ellenberger, Tom,Cusumano, Corinne K.,Hultgren, Scott J.,Janetka, James W.
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experimental part
p. 4779 - 4792
(2010/10/03)
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- Synthesis, biological activity of salidroside and its analogues
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Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs-Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl) methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.
- Guo, Yibing,Zhao, Yahong,Zheng, Cheng,Meng, Ying,Yang, Yumin
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experimental part
p. 1627 - 1629
(2011/02/24)
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- A simple, mild, and regioselective method for the benzylation of carbohydrate derivatives promoted by silver carbonate
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A simple, mild, and regioselective method has been developed for the selective benzylation and p-methoxybenzylation of carbohydrate derivatives in high yields using Ag2CO3 as the promoter. Benzylation of base-labile substrates, for w
- Malik, Satish,Dixit, Vaibhav A.,Bharatam, Prasad V.,Kartha, K.P. Ravindranathan
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experimental part
p. 559 - 564
(2010/10/04)
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- Synthesis, characterization and application study of two glycosides as flavour precursors
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Two glycosides of benzyl alcohol and phenethyl alcohol as flavour precursors have been synthesized and their structures were characterized by IR, 1H NMR spectra and ESI-MS. Their pyolysis products are investigated by the on-line pyrolysis gas chromatography-mass spectroscopy. Their transfer efficiency from tobacco to cigarette smoke was determined for evaluation of its possibility of application.
- Cai, Ji-Bao,Hui, Li,Shen, Xia,Su, Qing-De
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experimental part
p. 6647 - 6651
(2012/07/14)
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- Gold catalysis in glycosylation reactions
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Glycosylation of alcohols containing acid-sensitive groups, as for example 1,2-5,6-di-O-isopropylidene-glucofuranose, Fmoc-threonine tert-butyl ester or farnesol, is achieved using gly-cosyl trichloroacetimidates activated by gold(I) chloride (5-10 mol%). While glycosylation with 2-O-acyl protected glycosyl donors proceeds with 1,2-trans-selectivity, non-neighboring group active glycosyldonors give mixtures of anomeric glycosides or -glycosides depending upon their structure and the reactivity of the glycosyl acceptor. Georg Thieme Verlag Stuttgart New York.
- G?tze, Sebastian,Fitzner, Roland,Kunz, Horst
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scheme or table
p. 3346 - 3348
(2010/03/04)
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- [bmim][OTf]: a versatile room temperature glycosylation promoter
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[bmim][OTf] is a versatile, ionic liquid promoter for the room temperature glycosylation of both thiophenyl and trichloroacetimidate glycoside donors; the conditions are mild, with no requirement for molecular sieves, and are compatible with a wide range
- Galan, M. Carmen,Brunet, Claire,Fuensanta, Monica
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supporting information; body text
p. 442 - 445
(2009/05/27)
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- Synthesis of |β-(1→2)-linked oligomannosides
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β-(1→2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of |β-(1→2)-linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected β-(1→2)-linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development.
- Polakova, Monika,Roslund, Mattias U.,Ekholm, Filip S.,Saloranta, Tiina,Leino, Reko
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experimental part
p. 870 - 888
(2009/07/17)
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- Synthesis of DIvalent 2,2′-linked mannose derivatives by homodimerization
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Several studies have implicated (1 → 2)-linked mannans as biologically relevant compounds. Recently, there has been a growing interest in the synthesis of multivalent carbohydrate assemblies due to their ability to target multiple receptors simultaneously. In the present work, a protective group strategy, based on the methodology originally developed by Crich, has been utilized for the homodimerization of olefinic carbohydrates, allowing a highly diastereoselective synthesis of some divalent structures. Furthermore, it is shown that divalent donors may undergo coupling reactions without losses in stereoselectivity or efficiency. The strategies described may potentially be applied to the synthesis of diverse neoglycoconjugates and oligosaccharides. Georg Thieme Verlag Stuttgart.
- Ekholm, Filip S.,Polakova, Monika,Pawlowicz, Agnieszka J.,Leino, Reko
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experimental part
p. 567 - 576
(2009/07/18)
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- Stannyl ceramides as efficient acceptors for synthesising β-galactosyl ceramides
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β-Galactosyl ceramides have been obtained in excellent yields and stereoselectivities by reacting disarmed glycosyl donors with stannyl ethers. The broad compatibility of stannyl ethers with various leaving group-promoter pairs is demonstrated. The Royal
- Morales-Serna, Jose Antonio,Diaz, Yolanda,Matheu, M. Isabel,Castillon, Sergio
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body text
p. 3831 - 3836
(2009/02/05)
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- Highly efficient and stereoselective synthesis of β-glycolipids
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β-Galactosylceramide and glycolipid analogues were prepared in high yield and with complete chemo and stereoselectivity by reaction of α-iodo glycosides with stannyl ceramides, formed in situ. TBAI was used to activate both the iodogalactose and the stannyl ether. The Royal Society of Chemistry 2008.
- Morales-Serna, Jose Antonio,Boutureira, Omar,Diaz, Yolanda,Matheu, M. Isabel,Castillon, Sergio
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scheme or table
p. 443 - 446
(2008/10/09)
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- N-glycosyl amides as glycosyl donors in stereoselective glycosylation reactions
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Due to their high stability, N-glycosyl amides have so far not been considered as glycosyl donors for glycosylation reactions. Two new procedures for the cleavage of the anomeric amide functionality under mild reaction conditions and further stereoselecti
- Pleuss, Norbert,Kunz, Horst
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p. 122 - 130
(2007/10/03)
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- GC-MS characterization of acetylated O-glucofuranosides: Direct glucosylation of volatile alcohols from unprotected glucose
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O-Glucosylation of 1-pentanol, 1-octanol, 2-phenylethanol, benzyl alcohol, (±)-2-pentanol and (±)-menthol in 1,4-dioxane, using anhydrous FeCl3, afforded anomeric mixture of the corresponding glucofuranosides as major and glucopyranosides as minor products in overall yields 20-52 %. Practical advantages of GC-MS for characterizing the prepared acetylated glucofuranosides are in the focus of this paper. Glucofuranoside tetraacetate spectra contain characteristic signals of glucone (acetylated glucose) along with fragments of the aglucone moiety. The mass range was 50-600 mass units and acetyl ion was not present in the spectra, which is of interest for differentiating glucofuranoside and glucopyranoside tetraacetates.
- Jerkovic, Igor,Mastelic, Josip,Blazevic, Ivica,Sindler-Kulyk, Marija,Vikic-Topic, Drazen
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p. 313 - 318
(2007/10/03)
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- Selectively protected galactose derivatives for the synthesis of branched oligosaccharides
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Synthesis and characterization of several new anomerically pure galactose derivatives, based on simple and effective protective group manipulations of benzyl β-D-galactopyranoside, are reported. The monosaccharides described contain selectively protected/deprotected hydroxyl functionalities at their 1,2,3,4- and 6-positions rendering them useful as building blocks for construction of branched oligosaccharides.
- Lehtil?, Reko L.,Lehtil?, Juho O.,Roslund, Mattias U.,Leino, Reko
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p. 3653 - 3661
(2007/10/03)
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- GC-MS characterization of acetylated β-D-glucopyranosides: Transglucosylation of volatile alcohols using almond β-glucosidase
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β-D-Glucopyranosides of pentan-1-ol, (±)-pentan-2-ol, hexan-1-ol, octan-1-ol, benzyl alcohol, 2-phenylethanol, (±)-2-phenyl- propan-1-ol, 3-phenyl-propan-1-ol, geraniol and nerol were synthesized by transglucosylation of the respective alcohols with cellobiose using almond β-glucosidase. The reaction was carried out in acetonitrile with acetate buffer (vol. ratio 9:1), with the yields 14.4-45.0 %. Transglucosylation was not enantioselective. The products were characterized by GC-MS analysis of prepared tetraacetyl glucosides. Fragment ion characteristics of the aglucone moiety are present in all mass spectra, along with the fragments obtained from acetylated glucose. Acetylated glucosides are separable on HP-101 column (even diastereomeric tetraacetyl β-glucosides of enantiomeric alcohols).
- Jerkovic, Igor,Mastelic, Josip
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p. 529 - 535
(2007/10/03)
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- Synthesis of selected naturally occurring glucosides of volatile compounds. Their chromatographic and spectroscopic properties
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Naturally occurring glucosides of benzyl alcohol, (±)-menthol, (+)-borneol, thymol, carvacrol and eugenol were synthesized by the Koenigs-Knorr-Zemplen method (yields 19.5-52.2 %). Their β-D-glucopyranosidic structures were determined by one- and two-dimensional homo-and heteronuclear 1H and 13C NMR spectroscopy. The β-configuration was additionally confirmed by the hydrolysis with β-glucosidase. Tetraacetyl-β-D-glucopyranosides, as intermediates, were GC-MS analyzed. Diastereomeric β-glucoside tetraacetates of (±)-menthol were well separated on the HP-101 column. The mass spectra of glucopyranoside tetraacetates were mutually compared, as well as with the spectra of their aglycones.
- Mastelic, Josip,Jerkovic, Igor,Vinkovic, Marijana,Dzolic, Zoran,Vikic-Topic, Drazen
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p. 491 - 500
(2007/10/03)
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- InCl3.3H2O: An efficient Lewis acid catalyst for stereoselective O-glycosidation reactions of per-O-acetylglycopyranosyl trichloroacetimidates
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InCl3.3H2O catalysed highly stereoselective O-glycosidation of per-O-acetylglycopyranosyl trichloroacetimidates with a variety of aliphatic alcohols in dichloromethane at room temperature furnishes the corresponding glycosides in very good yields with excellent 1,2-trans stereoselectivity.
- Ghosh, Rina,Chakraborty, Arijit,Maiti, Dilip Kumar
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p. 602 - 604
(2007/10/03)
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- Synthesis of chloramphenicol and mandelonitrile galactose-containing prodrugs
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The synthesis of O1-β-D-galactopyranosylchloramphenicol and O1-β-D-galactopyranosylmandelonitrile as prodrugs potentially substrates of β-galactosidase, are reported. Preparation of O1-(2,3,4,6-tetra-O-acetyl-β-D-galactopy
- Janin, Yves L.,Zoltobroda, Gregory,Huel, Christiane,Monneret, Claude
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p. 275 - 286
(2007/10/03)
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- Elucidation of the mechanism of polysaccharide cleavage by chondroitin AC lyase from Flavobacterium heparinum
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Chondroitin AC lyase from Flavobacterium heparinum degrades chondroitin sulfate glycosaminoglycans via an elimination mechanism resulting in disaccharides or oligosaccharides with Δ4,5-unsaturated uronic acid residues at their nonreducing end. Mechanistic details concerning the ordering of the bond-breaking and -forming steps of this enzymatic reaction are nonexistent, mainly due to the inhomogeneous nature of the polymeric substrates. The creation of a new class of synthetic substrates for this enzyme has allowed the measurement of defined and reproducible kcat and Km values and has expanded the range of mechanistic studies that can be performed. The primary deuterium kinetic isotope effect upon kcat/Km for the abstraction of the proton α to the carboxylic acid was measured to be 1.67 ± 0.07, showing that deprotonation occurs in a rate-limiting step. Using substrates with leaving groups of differing reactivity, a flat linear free energy relationship was produced, indicating that the C4-O4 bond is not broken in a rate-determining step. Taken together, these results strongly suggest a stepwise mechanism. Consistent with this was the measurement of a secondary deuterium kinetic isotope effect upon kcat/Km of 1.01 ± 0.03 on a 4-{2H}-substrate, indicating that no sp2 character is developed at C4 during the rate-limiting step, thereby ruling out a concerted syn-elimination.
- Rye, Carl S.,Withers, Stephen G.
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p. 9756 - 9767
(2007/10/03)
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- A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid
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The synthesis of monomethyl-esterified trigalacturonans 1-3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired α-anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion.
- Clausen, Mads H.,Jorgensen, Malene R.,Thorsen, Jesper,Madsen, Robert
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p. 543 - 551
(2007/10/03)
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- Glycosides and phenylpropanoid glycerol in Vitis vinifera Cv. Gewurztraminer wine
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Eight glycosides and a phenylpropanoid glycerol were isolated from Vitis vinifera cv. Gewurztraminer wine, and their structures were elucidated by MS and NMR spectroscopies, cis-l-(5-Ethenyl-5methyltetrahydrofuran-2-yl)-l-methylethyl O-β-D-apiofuranosyl-(l→6)-Oβ-D-glucopyranoside, (E)3,6,9-trihydroxymegastigm-7-ene 9-O-β-D-glucopyranoside, 2-phenylethyl O-ss-D-apiofuranosyl-(1→6-O-β-D-glucopyranoside, and 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propane-1,3-diol are reported for the first time as wine components.
- Baltenweck-Guyot, Raymonde,Trendel, Jean-Michel,Albrecht, Pierre,Schaeffer, Alex
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p. 6178 - 6182
(2007/10/03)
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- Improved synthesis of 2,3:4,6-di-O-isopropylidene-D-glucopyranose and -D-galactopyranose
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2,3:4,6-Di-O-isopropylidene-D-glucopyranose and -D-galactopyranose acetals are conveniently prepared by hydrogenolysis of benzyl 2,3:4,6-di-O-isopropylidene-β-D-glucopyranose and -β-D-galactopyranose in almost quantitative yields in 3 h. This result is in contrast with the sluggish reaction observed (48 h) when the hydrogenolysis was carried out on either anomeric α,β mixtures or on the corresponding α anomers. Copyright (C) 1999 Elsevier Science Ltd.
- Gomez, Ana M.,Danelon, Gerardo O.,Valverde, Serafin,Lopez, J. Cristobal
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p. 138 - 142
(2007/10/03)
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