- Synthesis method of voglibose
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The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.
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Paragraph 0060- 0061; 0065-0067
(2021/08/07)
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- Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions
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A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.
- Dong, Hai,Feng, Guang-Jing,Guo, Yang-Fan,Liu, Chun-Yang,Luo, Tao
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- Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature
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A mild, convenient and transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presentedviaarynes generatedin situcombined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction conditions tolerate a variety of the pentoses and hexoses, and the reaction also performs smoothly on protected monosaccharides and disaccharides.
- Liao, Li-Hua,Liu, Yao,Yan, Nan,Yu, Xiao-Bing,Zhang, Xiang-Mei,Zhong, Qian
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p. 26666 - 26671
(2021/08/17)
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- Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts
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Herein, we report the oligopeptide-catalyzed site-selective acylation of partially protected monosaccharides. We identified catalysts that invert site-selectivity compared to N-methylimidazole, which was used to determine the intrinsic reactivity, for 4,6
- Seitz, Alexander,Wende, Raffael C.,Roesner, Emily,Niedek, Dominik,Topp, Christopher,Colgan, Avene C.,McGarrigle, Eoghan M.,Schreiner, Peter R.
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p. 3907 - 3922
(2021/03/09)
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- A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2
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Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti
- Ravinder, Mettu,Liao, Kuo-Shiang,Cheng, Yang-Yu,Pawar, Sujeet,Lin, Tzu-Lung,Wang, Jin-Town,Wu, Chung-Yi
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p. 15964 - 15997
(2020/11/13)
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- Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
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A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.
- Li, Zhongjun,Meng, Shuai,Yao, Wang,Zhong, Wenhe
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supporting information
(2020/04/09)
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- Synthesis of disaccharide modified berberine derivatives and their anti-diabetic investigation in zebrafish using a fluorescence-based technology
-
Berberine is a naturally occurring isoquinoline alkaloid and has been used as an important functional food additive in China due to its various pharmacological activities. Berberine exhibits great potential for developing anti-diabetic agents against type
- Jin, Meng,Kong, Haotian,Li, Xiaobin,Lin, Houwen,Liu, Kechun,Stoika, Rostyslav,Wang, Lizhen
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p. 3563 - 3574
(2020/05/25)
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- One-pot synthesis of cyclic oligosaccharides by the polyglycosylation of monothioglycosides
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Cyclic oligosaccharides such as cyclodextrins (CyDs) have been known as excellent host molecules for the inclusion of various organic guest molecules. The development of new synthetic methods for preparing cyclic oligosaccharides from simple and readily a
- Someya, Hidehisa,Seki, Takehito,Ishigami, Gota,Itoh, Taiki,Saga, Yutaka,Yamada, Yasuyuki,Aoki, Shin
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supporting information
(2019/12/14)
-
- Synthesis of type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of l-[U-13C6]-fucose for NMR binding studies
-
While 13C-labelled proteins are common tools in NMR studies, lack of access to 13C-labelled carbohydrate structures has restricted their use. l-Fucose is involved in a wide range of physiological and pathophysiological processes in mammalian organisms. He
- Lahmann, Martina,Long, Mark,Ní Cheallaigh, Aisling,Oscarson, Stefan,Reihill, Mark
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p. 4452 - 4458
(2020/10/20)
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- HEPARANASE COMPOUNDS AND METHODS OF USE
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The invention relates to compounds that interact with heparanase, uses in heparanase screening, uses in in vitro and in vivo imaging (e.g., positron emission tomography (PET) and magnetic resonance imaging (MRI)), methods of synthesis, methods of modulati
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-
Page/Page column 39-40
(2020/11/03)
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- Triflic acid-mediated synthesis of thioglycosides
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An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.
- Escopy, Samira,Singh, Yashapal,Demchenko, Alexei V.
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supporting information
p. 8379 - 8383
(2019/09/30)
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- Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
-
Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
- Keith, D. Jamin,Townsend, Steven D.
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supporting information
p. 12939 - 12945
(2019/08/22)
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- Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate
-
We described the chemical synthesis of a sulfated trisaccharide repeating unit of fucosylated chondroitin sulfate (FCS), which has significant anticoagulant activity. Well-functionalized monosaccharides were readily prepared, and highly efficient glycosyl
- He, Haiqing,Chen, Dong,Li, Xiaomei,Li, Chengji,Zhao, Jin-Hua,Qin, Hong-Bo
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supporting information
p. 2877 - 2882
(2019/03/21)
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- Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars
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A general protocol for functionalization of glycosyl thiols has been reported. This protocol is based on a single-electron Ni/photoredox dual-catalyzed cross coupling between 1-thiosugars and a broad range of aryl bromides and iodides as well as alkenyl and alkynyl halides. This base-free method gives access to a series of functionalized thioglycosides in moderate to excellent yields with a perfect control of the anomeric configuration. Moreover, it has been shown that this methodology may be transposed successfully to the continuous-flow photoredox chemistry.
- Zhu, Mingxiang,Dagousset, Guillaume,Alami, Mouad,Magnier, Emmanuel,Messaoudi, Samir
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supporting information
p. 5132 - 5137
(2019/07/03)
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- Synergistic Glycosylation as Key to the Chemical Synthesis of an Outer Core Octasaccharide of Helicobacter pylori
-
Helicobacter pylori, a widespread gastric bacterial pathogen that infects 90 % of the population in developing countries, causes chronic gastritis, peptic ulcers and gastric cancer. Battling H. pylori infection is a serious challenge due to the increased
- Zou, Xiaopeng,Qin, Chunjun,Pereira, Claney L.,Tian, Guangzong,Hu, Jing,Seeberger, Peter H.,Yin, Jian
-
supporting information
p. 2868 - 2872
(2018/02/06)
-
- Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography
-
Solid-phase synthesis is a practical approach for simplifying the time-consuming and routine purification steps in the preparation of numerous naturally occurring molecules; however, studying such reactions is difficult due to the lack of a convenient monitoring method. By using thin-layer chromatography in conjunction with a photolabile linker on a resin, we developed a convenient and simple method for monitoring solid-phase reactions in real time by thin-layer chromatography. This method provides a user-friendly protocol for examining reaction conditions for solid-state syntheses.
- Wu, Chia-Hui,Chen, Chun C.,Lin, Su-Ching,Wang, Cheng-Chung
-
supporting information
p. 1430 - 1436
(2018/05/15)
-
- Total Synthesis of Nucleoside Antibiotics Plicacetin and Streptcytosine A
-
Disaccharide nucleoside antibiotics plicacetin and streptcytosine A (also named rocheicoside A) were effectively synthesized through the common precursor cytosamine. The amosamine and amicetose moieties were efficiently assembled through an α-selective O-
- Fu, Jiqiang,Laval, Stephane,Yu, Biao
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p. 7076 - 7084
(2018/07/15)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.
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-
-
- Immobilization of UDP-Galactose on an Amphiphilic Resin
-
Nucleotide sugars are activated sugar precursors used by glycosyltransferases to form glycans. Here we report the first examples of resin-bound nucleotide sugars: fluorinated UDP-galactose and UDP-galactose. They were conjugated to a polyethylene glycol resin through the C6 position with an SMCC linker in good to excellent yields. This synthesis represents an efficient method to access resin-bound nucleotide sugars in a modular approach that enables modifications of the sugar or nucleotide before conjugation. The system has been conceived as a new chemistry-based screening system for enzymes that use UDP-galactose.
- Bevan, Jessica G. M.,Louren?o, Eva C.,Chaves-Ferreira, Miguel,Rodrigues, Jo?o A.,Rita Ventura
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supporting information
p. 908 - 914
(2018/02/27)
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- InBr 3 -Catalyzed Synthesis of Aryl 1,2- trans -Thio(seleno)glycosides
-
InBr 3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2- t
- Ma, Teng,Li, Changwei,Liang, Haijing,Wang, Zhaoyan,Yu, Lan,Xue, Weihua
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supporting information
p. 2311 - 2314
(2017/10/06)
-
- Synthesis of Chondroitin Sulfate A Bearing Syndecan-1 Glycopeptide
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Syndecan-1 chondroitin sulfate glycopeptide was synthesized for the first time using the cassette approach. The sequence of glycosylation to form the octasaccharide serine cassette was critical. The glycopeptide was successfully assembled via a 2+ (3 + 3)
- Ramadan, Sherif,Yang, Weizhun,Zhang, Zeren,Huang, Xuefei
-
supporting information
p. 4838 - 4841
(2017/09/23)
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- NOVEL NEISSERIA MENINGITIDIS SEROGROUP Y OLIGOMER AND PROCESS FOR SYNTHESIZING THEREOF
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The present invention relates to novel oligomers of Neisseria meningitidis serogroup Y capsular polysaccharide repeating unit (Men-Y oligomers) and process for synthesizing novel Men- Y oligomers. In particular, the present invention relates to the chemic
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-
Page/Page column 12; 20
(2017/02/24)
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- PREPARATION OF MONOSACCHARIDES, DISACCHARIDES, TRISACCHARIDES, AND PENTASACCHARIDES OF HEPARINOIDS
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The present invention provides preparations of monosaccharides, disaccharides, trisaccharides, and pentasaccharides of heparinoids. The present invention also provides novel monosaccharides, disaccharides, trisaccharides and pentasaccharides for use in th
- -
-
Paragraph 0124; 0125
(2017/02/02)
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- Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
-
A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.
- Singh, Adesh Kumar,Tiwari, Varsha,Mishra, Kunj Bihari,Gupta, Surabhi,Kandasamy, Jeyakumar
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supporting information
p. 1139 - 1144
(2017/06/20)
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- Efficient Divergent Synthesis of New Immunostimulant 4″-Modified α-Galactosylceramide Analogues
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A synthesis strategy for the swift generation of 4″-modified α-galactosylceramide (α-GalCer) analogues is described, establishing a chemical platform to comprehensively investigate the structure-activity relationships (SAR) of this understudied glycolipid
- Janssens, Jonas,Decruy, Tine,Venken, Koen,Seki, Toshiyuki,Krols, Simon,Van Der Eycken, Johan,Tsuji, Moriya,Elewaut, Dirk,Van Calenbergh, Serge
-
supporting information
p. 642 - 647
(2017/06/13)
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- Determining Substrate Specificities of β1,4-Endogalactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly
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Pectin is a structurally complex plant polysaccharide with many industrial applications in food products. The structural elucidation of pectin is aided by digestion assays with glycosyl hydrolases. We report the automated glycan assembly of oligosaccharid
- Bartetzko, Max P.,Schuhmacher, Frank,Seeberger, Peter H.,Pfrengle, Fabian
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supporting information
p. 1842 - 1850
(2017/02/10)
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- Anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and preparation method thereof
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The invention relates to an anthrax capsule surface carbohydrate antigen-based novel trisaccharide 4-methoxyphenoside compound and a preparation method thereof. The structural formula of the trisaccharide 4-methoxyphenoside compound is shown in the description; and in the formula, R1 is an acetyl group, R2 is a benzyl group, R3 is an acetamido group, and the end position is a p-methylphenoxyl group. The compound can be used for preparing oligosaccharide-like conjugates, can be used for synthesis reaches of anthrax carbohydrate vaccines, has the advantages of concise synthesis route, simplicity in operation, low raw material cost, strong versatility, and good glycosylation reaction stereoselectivity, and is suitable for synthesizing various oligosaccharide compounds.
- -
-
Paragraph 0043; 0045
(2017/06/02)
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- A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa
-
Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained wi
- Li, Cui-yun,Liu, Guang-jian,Du, Wei,Zhang, Yuan,Xing, Guo-wen
-
supporting information
p. 2109 - 2112
(2017/05/09)
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- Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery
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Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(IV) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(IV) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 μM) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.
- Ma, Jing,Wang, Qingpeng,Huang, Zhonglv,Yang, Xiande,Nie, Quandeng,Hao, Wenpei,Wang, Peng George,Wang, Xin
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supporting information
p. 5736 - 5748
(2017/07/22)
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- Oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, preparation method and applications thereof
-
The present invention relates to an oligosaccharide conjugate based on Streptococcus pneumoniae type 3 capsular polysaccharide, a preparation method and applications thereof, wherein the structure general formula of the oligosaccharide conjugate is define
- -
-
Paragraph 0057; 0058; 0059
(2017/10/13)
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- Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3
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Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.
- Weng, Shiue-Shien,Hsieh, Kun-Yi,Zeng, Zih-Jian
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p. 464 - 473
(2017/05/19)
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- Total synthesis of mangiferin, homomangiferin, and neomangiferin
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Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.
- Wei, Xiong,Liang, Danlin,Wang, Qing,Meng, Xiangbao,Li, Zhongjun
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supporting information
p. 8821 - 8831
(2016/10/03)
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- THIOALDOHEXOSE DERIVATIVE AND METHOD FOR PRODUCING SAME
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PROBLEM TO BE SOLVED: To provide novel synthesis methods and novel intermediates of 3-(6-deoxysulfoaldohexose)-1-propanol derivatives. SOLUTION: The present invention provides a thioaldohexose derivative represented by the formula (III) where R is an optionally substituted alkyl group or an optionally substituted aryl group, R21, R31 and R41 are the same or different to represent a protective group of a hydroxy group, and -OR61 is a leaving group. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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-
Paragraph 0043; 0044; 0046
(2018/09/02)
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- A Sugar-Based Gelator for Marine Oil-Spill Recovery
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Marine oil spills constitute an environmental disaster with severe adverse effects on the economy and ecosystem. Phase-selective organogelators (PSOGs), molecules that can congeal oil selectively from oil–water mixtures, have been proposed to be useful for oil-spill recovery. However, a major drawback lies in the mode of application of the PSOG to an oil spill spread over a large area. The proposed method of using carrier solvents is impractical for various reasons. Direct application of the PSOG as a solid, although it would be ideal, is unknown, presumably owing to poor dispersion of the solid through the oil. We have designed five cheap and easy-to-make glucose-derived PSOGs that disperse in the oil phase uniformly when applied as a fine powder. These gelators were shown to selectively congeal many oils, including crude oil, from oil–water mixtures to form stable gels, which is an essential property for efficient oil-spill recovery. We have demonstrated that these PSOGs can be applied aerially as a solid powder onto a mixture of crude oil and sea water and the congealed oil can then be scooped out. Our innovative mode of application and low cost of the PSOG offers a practical solution to oil-spill recovery.
- Vibhute, Amol M.,Muvvala, Venkatanarayana,Sureshan, Kana M.
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supporting information
p. 7782 - 7785
(2016/07/07)
-
- An investigation of construction of chondroitin sulfate E (CS-E) repeating unit
-
A series of the derivatives of chondroitin sulfate E (CS-E) disaccharide repeating unit were prepared by postglycosylation–oxidation strategy. The strategy showed excellent performance in glycosylation both on the reactivity and stereoselectivity. Different protecting methodologies were used for the manipulation of disaccharide building blocks. Substitutes at C-4 of glucosyl donors mildly influenced the glycosylation. The current synthesis afforded a feasible approach for the preparation of CS-E repeating unit.
- Yang, Shuang,Wang, A-peng,Zhang, Guangyan,Di, Xiangjie,Zhao, Zhehui,Lei, Pingsheng
-
supporting information
p. 5659 - 5670
(2016/08/23)
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- HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
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Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.
- -
-
Paragraph 0241
(2016/05/10)
-
- TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
-
The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.
- Hsu, Mei-Yuan,Liu, Yi-Pei,Lam, Sarah,Lin, Su-Ching,Wang, Cheng-Chung
-
supporting information
p. 1758 - 1764
(2016/10/05)
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- Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2
-
A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.
- Mukherjee, Mana Mohan,Basu, Nabamita,Chaudhury, Aritra,Ghosh, Rina
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p. 109301 - 109314
(2016/11/30)
-
- Solvent-free bismuth oxycarbonate-mediated mechanochemical glycosylation: A simple greener alternative to access O-/S-glycosides efficiently
-
Preparation of a variety of per-O-acylated O- and S-glycosides of a set of commonly encountered mono- and disaccharides has been achieved effectively by solvent-free grinding of the corresponding acetylated/benzoylated glycosyl bromide and the desired acceptor alcohol/thiol in the presence of bismuth carbonate in a planetary ball mill. The method is simple, requires short reaction time periods and is practical allowing it to be performed at a milligram-to multi-gram scale as required. In the cases where the product is crystalline, it was often obtained in practically pure form by crystallization (and without the need for chromatographic isolation).
- Sethi, Kashmir Prasad,Kartha, K.P. Ravindranathan
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p. 132 - 135
(2016/09/23)
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- A Kinsenoside and GoodyerosideA analogs of the preparation and use thereof
-
The invention discloses a preparation method and application of compounds as shown in formula I and II, and in particular relates to preparation of Kinsenoside or GoodyerosideA analogue and medical application of the Kinsenoside or GoodyerosideA analogue
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-
Paragraph 0035; 0036; 0037; 0038; 0039
(2017/06/14)
-
- Preparation 2, 3, 4, 6-tetra-O-benzyl-D-pyran semi-acetyllactosyl method
-
The invention relates to the field of saccharide compounds, particularly a method for preparing 2,3,4,6-tetra-oxy-benzyl-D-galactopyranose. The method comprises the following steps: preparing benzothiazolyl thioacetyl galactose from galactose under the ac
- -
-
Paragraph 0044-045
(2017/02/17)
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- Total Synthesis of Myrmekioside A, a Mono-O-alkyl-diglycosylglycerol from Marine Sponge Myrmekioderma sp.
-
Myrmekioside A, which was isolated from the marine sponge Myrmekioderma sp. as a member of the family of natural mono-O-alkyl-diglycosylglycerols, and which has a strong reversion effect on the tumor cell morphology of ras-transformed cells at 5 μg/mL, wa
- Zhang, Jun,Li, Chunxia,Sun, Linlin,Yu, Guangli,Guan, Huashi
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p. 4246 - 4253
(2015/06/30)
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- HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
-
Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and exp
- -
-
Paragraph 0243-0245
(2015/03/16)
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- Automated Glycan Assembly of Oligosaccharides Related to Arabinogalactan Proteins
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Arabinogalactan proteins are heavily glycosylated proteoglycans in plants. Their glycan portion consists of type-II arabinogalactan polysaccharides whose heterogeneity hampers the assignment of the arabinogalactan protein function. Synthetic chemistry is
- Bartetzko, Max P.,Schuhmacher, Frank,Hahm, Heung Sik,Seeberger, Peter H.,Pfrengle, Fabian
-
supporting information
p. 4344 - 4347
(2015/09/15)
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- Cu(ClO4)2·6H2O catalyzed solvent free per-O-acetylation and sequential one-pot conversions of sugars to thioglycosides
-
The solvent free per-O-acetylation of various reducing and non-reducing sugars has been carried out using stoichiometric amounts of acetic anhydride and copper(ii) perchlorate hexahydrate as the catalyst. The reactions with various reducing monosaccharides have also been followed by a one-pot sequential conversion to the corresponding thioglycosides in high yields. This journal is
- Chatterjee, Debnath,Paul, Abhijit,Rajkamal,Yadav, Somnath
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p. 29669 - 29674
(2015/05/20)
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- Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature
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A general and efficient protocol for the palladium-catalyzed functionalization of mono- and polyglycosyl thiols by using the palladacycle precatalyst G3-XantPhos was developed. The C-S bond-forming reaction was achieved rapidly at room temperature with various functionalized (hetero)aryl-, alkenyl-, and alkynyl halides. The functional group tolerance on the electrophilic partner is typically high and anomer selectivities of thioglycosides are high in all cases studied. New sulfur nucleophiles such as thiophenols, alkythiols, and thioaminoacids (cysteine) were also successfully coupled to lead to the most general and practical method yet reported for the functionalization of thiols.
- Bruneau, Alexandre,Roche, Maxime,Hamze, Abdallah,Brion, Jean-Daniel,Alami, Mouad,Messaoudi, Samir
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p. 8375 - 8379
(2015/06/02)
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- Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4'-deoxy-4'-fluoro-Thomsen-Friedenreich epitope
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The development of selective anticancer vaccines that provide enhanced protection against tumor recurrence and metastasis has been the subject of intense research in the scientific community. The tumor-associated glycoprotein MUC1 represents a well-established target for cancer immunotherapy and has been used for the construction of various synthetic vaccine candidates. However, many of these vaccine prototypes suffer from an inherent low immunogenicity and are susceptible to rapid in vivo degradation. To overcome these drawbacks, novel fluorinated MUC1 glycopeptide-BSA/TTox conjugate vaccines have been prepared. Immunization of mice with the 4'F-TF-MUC1-TTox conjugate resulted in strong immune responses overriding the natural tolerance against MUC1 and producing selective IgG antibodies that are cross-reactive with native MUC1 epitopes on MCF-7 human cancer cells.
- Johannes, Manuel,Reindl, Maximilian,Gerlitzki, Bastian,Schmitt, Edgar,Hoffmann-R?der, Anja
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supporting information
p. 155 - 161
(2015/02/05)
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- Exploring glycosylation reactions under continuous-flow conditions
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The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.
- Cancogni, Damiano,Lay, Luigi
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supporting information
p. 2873 - 2878
(2015/01/16)
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- Total synthesis of anticoagulant pentasaccharide fondaparinux
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The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor the process of total synthesis of fondaparinux were employed. This work provides a comprehensive elaboration for the synthesis and analysis of fondaparinux based on related literature, as well as abundant information for the synthesis of heparin-like oligosaccharides. A matter of protection! The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy. The process of total synthesis was monitored by HPLC and NMR. This work will contribute to continued improvement of the multistep production of fondaparinux and provide abundant information for the synthesis of heparin-like oligosaccharides.
- Li, Tiehai,Ye, Hui,Cao, Xuefeng,Wang, Jiajia,Liu, Yonghui,Zhou, Lifei,Liu, Qiang,Wang, Wenjun,Shen, Jie,Zhao, Wei,Wang, Peng
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p. 1071 - 1080
(2014/05/20)
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- Useful approach to the synthesis of aryl thio- and selenoglycosides in the presence of rongalite
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A simple, mild, and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate a chalcogenide anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-d-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.
- Venkateswarlu, Cheerladinne,Gautam, Vibha,Chandrasekaran, Srinivasan
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