- Aspartic Acid Forming α-Ketoacid-Hydroxylamine (KAHA) Ligations with (S)-4,4-Difluoro-5-oxaproline
-
The α-ketoacid-hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. Currently, the most applied hydroxylamine is the 5-membered cyclic hydroxylamine (S)-5-oxaproline, which forms a homoserine ester as the primary ligation product. In order to access native aspartic acid residues at the ligation site, we synthesized a 4,4-difluoro version of this monomer. Upon KAHA ligation, the resulting difluoro alcohol hydrolyzes to an aspartic acid residue with little or no formation of aspartamide. We applied this monomer for the synthesis of the hormone peptides glucagon and an insulin variant, and as well for segment ligation of the peptides UbcH5a and SUMO3.
- Baldauf, Simon,Bode, Jeffrey W.,Boross, Gábor N.,Ogunkoya, Ayodele O.
-
-
- Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides
-
A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.
- Li, Ming,Qiu, Yi-Feng,Wang, Cui-Tian,Li, Xue-Song,Wei, Wan-Xu,Wang, Yu-Zhao,Bao, Qiao-Fei,Ding, Ya-Nan,Shi, Wei-Yu,Liang, Yong-Min
-
supporting information
p. 6288 - 6293
(2020/09/02)
-
- Total Synthesis of 6-Amino-2,6-dideoxy-α-Kdo from d -Mannose
-
3-Deoxy-d-manno-oct-2-ulosonic acid (Kdo) biosynthetic pathway is a promising target in antibacterial drug discovery. Herein, we report the total synthesis of 6-amino-2,6-dideoxy-α-Kdo in 15 steps from d-mannose as a potential inhibitor of Kdo-processing
- Ameur, Nassima,Gamboa Marin, Oscar Javier,Gauthier, Charles,Gormand, Paul,Hussain, Nazar,Ravicoularamin, Gokulakrishnan,Sauvageau, Janelle
-
supporting information
(2020/07/27)
-
- Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues
-
Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.
- Carell, Thomas,Ensfelder, Timm T.,Heiss, Matthias,Hillmeier, Markus,Kellner, Stefanie,Müller, Markus,Michalakis, Stylianos,Sch?n, Alexander,Scheel, Constanze,Thumbs, Peter,Wagner, Mirko
-
supporting information
p. 12352 - 12356
(2020/04/27)
-
- Discovery and Structure-Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δModulators
-
Following our report that A3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′-homologated adenosine analogues 4a-4t, as dual PPARγ/δmodulators without AR binding. Removal of binding affinity to A3AR was achieved by 1′-homologation, and PPARγ/δdual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δbut lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγaffinity, indicating that the C2 position defines a pharmacophore for selective PPARγligand designs. PPARγ/δdual modulators functioning as both PPARγpartial agonists and PPARδantagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.
- An, Seungchan,Kim, Gyudong,Kim, Hyun Jin,Ahn, Sungjin,Kim, Hyun Young,Ko, Hyejin,Hyun, Young Eum,Nguyen, Mai,Jeong, Juri,Liu, Zijing,Han, Jinhe,Choi, Hongseok,Yu, Jinha,Kim, Ji Won,Lee, Hyuk Woo,Jacobson, Kenneth A.,Cho, Won Jea,Kim, Young-Mi,Kang, Keon Wook,Noh, Minsoo,Jeong, Lak Shin
-
p. 16012 - 16027
(2021/01/09)
-
- Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals
-
A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy
- Choutka, Jan,Kratochvíl, Michal,Parkan, Kamil,Pohl, Radek,Zyka, Jakub
-
supporting information
(2020/08/24)
-
- PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING GLAUCOMA, CONTAINING ADENOSINE DERIVATIVE
-
A pharmaceutical composition for preventing or treating eye diseases and an oral administration agent for preventing or treating eye diseases are provided. The pharmaceutical composition for preventing or treating eye diseases comprises the compound repre
- -
-
Paragraph 0126-0130
(2020/02/05)
-
- Synthesis of Bioactive Side-Chain Analogues of TAN-2483B
-
The fungal metabolite TAN-2483B has a 2,6-trans-relationship across the pyran ring of its furo[3,4-b]pyran-5-one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side-chain
- Somarathne, Kalpani K.,McCone, Jordan A. J.,Brackovic, Amira,Rivera, José Luis Pinedo,Fulton, J. Robin,Russell, Euan,Field, Jessica J.,Orme, Christopher L.,Stirrat, Hedley L.,Riesterer, Jasmin,Teesdale-Spittle, Paul H.,Miller, John H.,Harvey, Joanne E.
-
p. 1230 - 1237
(2019/02/07)
-
- Compound, preparation method and applications thereof, and glycosidase inhibitor
-
The invention relates to the field of enzyme inhibitors, and discloses a compound, a preparation method and applications thereof, and a glycosidase inhibitor, wherein the compound has a structure represented by a formula (I), R is any one selected from hy
- -
-
Paragraph 0068-0071
(2019/10/01)
-
- Synthesis of Butenolides via a Horner-Wadsworth-Emmons Cascading Dimerization Reaction
-
The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner-Wadsworth-Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes f
- Everson, Jack,Kiefel, Milton J.
-
p. 15226 - 15235
(2019/11/21)
-
- PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING NONALCOHOLIC STEATOHEPATITIS, HEPATIC FIBROSIS, AND LIVER CIRRHOSIS, COMPRISING ADENOSINE DERIVATIVES
-
A pharmaceutical composition for preventing or treating liver disease is provided. The pharmaceutical composition comprising a compound represented by formula 1 below or a pharmaceutically acceptable salt of the compound as an active ingredient: where A i
- -
-
Paragraph 0082
(2019/09/15)
-
- PHOSPHORYLATED HEPTOSE COMPOUNDS : PROCESS FOR THEIR PREPARATION AND USE
-
Processes for the preparation of phosphorylated heptose compounds are provided. Embodiments of the invention relate to the chemical synthesis of heptopyranose phosphate compounds. Also, embodiments of the invention relate to the use of compounds according
- -
-
Paragraph 0079
(2018/12/03)
-
- Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity
-
[Figure not available: see fulltext.] Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.
- Halay, Erkan,Ay, Emriye,?alva, Emine,Ay, Kadir,Karay?ld?r?m, Tamer
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p. 158 - 166
(2018/04/02)
-
- Synthesis, characterization and physicochemical analysis of some mannofuranoside derivatives with potent antimicrobial activity
-
We have synthesized protected mannofuranose as a glycosyl donor and some heterocyclic moieties as glycosyl acceptor. Coupling of glycosyl donor and acceptor by glycosylation, results in the formation of mannofuranoside derivatives. Antimicrobial potential of synthesized compounds were tested against five different human pathogenic bacteria and two fungi by using microdilution method. Interestingly, all synthesized mannofuranoside derivatives gave antimicrobial activity. Cumulatively, inhibitory concentration (IC50) against bacteria were found to be in the range of 84.28-309.43 μg/ml, while, IC50 against fungus were in the range of 0.59-3.82 mg/ml. Ampicillin and Fluconazole were used as positive control. Further, physicochemical parameters of synthesized mannofuranoside derivatives were analyzed using in-silico approach. Fortunately, none of our synthesized mannofuranoside derivatives gave violation of Lipinski’s Rule of Five. Thus, we can safely state that these synthesized mannofuranoside derivatives could be considered as potential anti-microbial drug candidates.
- Hassan, Firoj,Nasibullah, Malik,Ahmad, Naseem,Kamal, Azhar,Danish Rizvi, Syed Mohd,Khan, Mohd Sajid,Khan, Abdul Rahman
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p. 2731 - 2741
(2018/02/20)
-
- Alternate synthesis to D-glycero-β-D-manno-heptose 1,7-biphosphate
-
D-glycero-β-D-manno-heptose 1,7-biphosphate (HBP) is an enzymatic intermediate in the biosynthesis of the heptose component of lipopolysaccharide (LPS), and was recently revealed to be a pathogen-associated molecular pattern (PAMP) that allows detection o
- Sauvageau, Janelle,Bhasin, Milan,Guo, Cynthia X.,Adekoya, Itunuoluwa A.,Gray-Owen, Scott D.,Oscarson, Stefan,Guazzelli, Lorenzo,Cox, Andrew
-
-
- A sulfur-containing thick mixed four ring aza sugar derivative and its preparation method
-
The invention discloses a sulfur-containing thick and mixed tetracyclic azasugar derivative, which has a general chemical formula as shown in figure I. A preparation method of the sulfur-containing thick and mixed tetracyclic azasugar derivative comprises
- -
-
Paragraph 0038; 0041; 0042
(2017/08/15)
-
- Synthesis of Iminosugar-Containing KRN7000 Analogues
-
Three new iminosugar-containing KRN7000 (also referred to as α-GalCer) analogues were designed and synthesized. In the design, the galactose moiety of KRN7000 was replaced by iminosugars and the iminosugar structures were connected with ceramide in differ
- Zhang, Lei,Ye, Xin-Shan
-
p. 1001 - 1008
(2017/06/27)
-
- Undemanding Synthesis of Novel C19 and C17 Analogues of C18-Guggultetrol
-
A simple and undemanding synthesis of (2S,3R,4R,5R)-nonadecane-1,2,3,4,5-pentol and (2S,3R)-heptadecane-1,2,3-triol as novel C19 and C17 analogues of C18-guggultetrol was achieved by using l-ascorbic acid as a chiral pool.
- Dhage, Ganesh R.,Thopate, Shankar R.
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p. 970 - 972
(2017/05/05)
-
- Click Inspired Synthesis of 1,2,3-Triazole-linked 1,3,4-Oxadiazole Glycoconjugates
-
The glycoconjugation of biologically privileged 1,3,4-oxadiazole scaffold is described via Cu(I)-catalyzed azide–alkyne cycloaddition. A series of glycosyl alkynes 1b–i, obtained from various commercial sugars, were treated with azide functionalized 1,3,4-oxadiazole using click chemistry to access triazole-linked glycosylated 1,3,4-oxadiazoles 10b–i in good yields. The structure of the developed glycoconjugates has been ascertained by extensive spectroscopic analysis (1H &13C NMR, IR, and MS).
- Kushwaha, Divya,Tiwari, Vinod K.
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p. 2454 - 2462
(2017/07/25)
-
- Practical preparation of mono- and di-O-isopropylidene derivatives of monosaccharides and methyl 4,6-O-benzylidene glycosides from free sugars in a deep eutectic solvent
-
Free sugars were rapidly converted into the corresponding di-O-isopropylidene derivatives and methyl O-benzylidene glycosides in excellent yields and purity in a deep eutectic solvent made from choline chloride and malonic acid (ChCl:MA). Reaction conditions were mild; work-up was easy, and further purification was not necessary. Given the inexpensive, nontoxic, and recyclable nature of ChCl:MA, this protocol is environmental friendly.
- Rokade, Sunil M.,Bhate, Prakash M.
-
-
- Synthesis of oxylipin mimics and their antifungal activity against the citrus postharvest pathogens
-
Nine oxylipin mimics were designed and synthesized starting from D-mannose. Their antifungal activity against three citrus postharvest pathogens was evaluated by spore germination assay. The results indicated that all the compounds significantly inhibited the growth of Penicillium digitatum, Penicillium italicum and Aspergillus Niger. The compound (3Z,6Z,8S,9R,10R)-octadeca-3,6-diene-8,9,10-triol (3) exhibited excellent inhibitory effect on both Penicillium digitatum (IC50 = 34 ppm) and Penicillium italicum (IC50 = 94 ppm). Their in vivo antifungal activities against citrus postharvest blue mold were tested with fruit inoculated with the pathogen Penicillium italicum. The compound (3R,4S)-methyl 3,4-dihydroxy-5-octyltetrahydrofuran-2-carboxylate (9) demonstrated significant efficacy by reducing the disease severity to 60%. The antifungal mechanism of these oxylipin mimics was postulated in which both inhibition of pathogenic mycelium and stimuli of the host oxylipin-mediated defense response played important roles.
- Ma, Jimei,Li, Yupeng,Chen, Hangwei,Zeng, Zhen,Li, Zi-Long,Jiang, Hong
-
-
- Efficient Large Scale Syntheses of 3-Deoxy- d -manno-2-octulosonic acid (Kdo) and Its Derivatives
-
An efficient method to rapidly synthesize 3-deoxy-d-manno-2-octulosonic acid (Kdo) and its derivatives in large scale has been developed. Starting from d-mannose, the di-O-isopropylidene derivative of Kdo ethyl ester was prepared in three steps on a scale of more than 40 g in one batch in an overall yield of 75-80% without any intermediate purification. Kdo, Kdo glycal, and 2-acetylated Kdo ester were synthesized quickly in high yield from a di-O-isopropylidene derivative of Kdo ethyl ester. 2-Deoxy-β-Kdo ester was obtained with high stereoselectivity via the epimerization of the α-isomer using t-BuOH as a proton source.
- Feng, Yingle,Dong, Jie,Xu, Fangyuan,Liu, Aiyun,Wang, Li,Zhang, Qi,Chai, Yonghai
-
supporting information
p. 2388 - 2391
(2015/05/27)
-
- Lead tetraacetate mediated one pot oxidative cleavage and acetylation reaction: an approach to apio and homologated apio pyrimidine nucleosides and their anticancer activity
-
An efficient and versatile strategy of general applicability towards apio and homologated apio pyrimidines has been delineated. The methodology shows tosylation followed by in situ cyclization and one pot oxidative cleavage and acetylation by Pb(OAc)4 as the key steps. The methodology has been applied to d-ribose and d-mannose derivatives to achieve asymmetric synthesis of apio and homologated apio pyrimidine nucleosides.
- Panda, Amarendra,Islam, Sehbanul,Santra, Manas Kumar,Pal, Shantanu
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p. 82450 - 82459
(2015/10/12)
-
- Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
-
Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
- Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
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p. 11023 - 11028
(2014/03/21)
-
- C-Triazolyl β-d-furanosides as LpxC inhibitors: Stereoselective synthesis and biological evaluation
-
C-Triazolyl β-d-furanosides 10a-f were synthesized in a stereocontrolled way, starting from d-mannose. In the key steps of the synthesis a diastereoselective reduction of hemiketal 14 and a Cu(I) catalyzed [3+2]-cycloaddition of central building block 18
- Jana, Sunit Kumar,L?ppenberg, Marius,Daniliuc, Constantin G.,Holl, Ralph
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p. 6569 - 6577
(2015/03/30)
-
- CARBOHYDRATE PHOSPHONATE DERIVATIVES AS MODULATORS OF GLYCOSYLATION
-
Compounds of Formula (I) are useful as modulators of glycosylation. Compounds of Formula (I) have the following structure: (I) and the definitions of the other variables are provided herein.
- -
-
Paragraph 0108
(2014/09/03)
-
- GLYCOSIDASE INHIBITORS AND USES THEREOF
-
The invention provides compounds for inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.
- -
-
Paragraph 00170
(2014/03/25)
-
- A highly efficient catalyst for selective oxidative scission of olefins to aldehydes: Abnormal-NHC-Ru(II) complex in oxidation chemistry
-
The utility and selectivity of the catalyst [Ru(COD)(L1)Br2] (1) bearing a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based abnormal N-heterocyclic carbene ligand L1 is demonstrated toward selective oxidation of C=C bonds to aldehydes and C=C bonds to α-diketones in an EtOAc/CH3CN/H2O solvent mixture at room temperature using a wide range of substrates, including highly functionalized sugar- and amino acid-derived compounds.
- Daw, Prosenjit,Petakamsetty, Ramu,Sarbajna, Abir,Laha, Siladitya,Ramapanicker, Ramesh,Bera, Jitendra K.
-
supporting information
p. 13987 - 13990
(2015/01/08)
-
- Design, synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity
-
A new series of novel benzimidazole derivatives containing substituted pyrid-2-yl moiety and polyhydroxy sugar conjugated to the N-benzimidazole moiety has been synthesized and evaluated as orally bioavailable anti-inflammatory agents with anti-ulcerogenic activity. The anti-inflammatory and anti-ulcerogenic activities of these compounds were compared to diclofenac and omeprazole, respectively. In carrageenan-induced paw oedema assay, 2-methyl-N-((3,4-dimethoxypyridin-2-yl)methyl)-1H-benzimidazol-5-amine (12d) and 1-(1,2,3,5-tetrahydroxy-α-d-mannofuranose)-5-(((3,4-dimethoxypyridin-2yl) methyl)amino)-2-methyl-1H-benzimidazole (15d) displayed dose-dependent anti-inflammatory activities by decreasing the inflammation by 62% and 72%, respectively which is comparable to that of diclofenac (73%). In contrast to diclofenac, the anti-inflammatory activity of these compounds was not only free from any side effects on the gastric mucosa but also showed significant anti-ulcerogenic activity in rat pyloric ligation and ethanol-induced gastric ulcer models similar to that of omeprazole. Together, these findings suggest that 12d and 15d are potent anti-inflammatory agents with concurrent anti-ulcerogenic activity and support its clinical promise as a component of therapeutic strategies for inflammation, for which the gastric side effects are always a major limitation.
- El-Nezhawy, Ahmed O.H.,Biuomy, Ayman R.,Hassan, Fatma S.,Ismaiel, Ayman K.,Omar, Hany A.
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p. 1661 - 1670
(2013/05/09)
-
- Development of novel LpxC inhibitors: Chiral-pool synthesis of C-triazolyl glycosides
-
The Zn2+-dependent deacetylase LpxC plays an important role in the biosynthesis of the cell wall of Gram-negative bacteria and therefore represents an interesting target for the development of novel antibiotics. In a 10-step, chiral pool synthe
- Jana, Sunit Kumar,L?ppenberg, Marius,Daniliuc, Constantin G.,Jose, Joachim,Holl, Ralph
-
p. 9434 - 9442
(2013/10/08)
-
- Design and stereoselective synthesis of a C-aryl furanoside as a conformationally constrained CHIR-090 analogue
-
The UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) is a promising target for the development of novel antibiotic substances against multidrug-resistant Gram-negative bacteria. The C-aryl glycoside 3 was designed as conformationally constrained analogue of the potent LpxC-inhibitor CHIR-090. The chiral pool synthesis of 3 started with d-mannose. The C-aryl glycoside 8 was synthesized stereoselectively by nucleophilic attack of 4-iodine-substituted phenyllithium and subsequent reduction with Et 3SiH. The ester 10 was obtained in a one-pot diol cleavage, CrO 3 oxidation, and esterification. A Sonogashira reaction of the aryl iodide 11 led to the alkyne 17 which was transformed with H2NOH into the hydroxamic acid 3.
- Oddo, Alberto,Holl, Ralph
-
p. 59 - 64,6
(2020/08/31)
-
- A chiron approach to aminocytitols by petasis-borono-mannich reaction: Formal synthesis of (+)-conduramine e and (-)-conduramine e
-
A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-β-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.
- Ghosal, Partha,Shaw, Arun K.
-
supporting information
p. 7627 - 7632,6
(2020/08/24)
-
- Synthesis of N-homobicyclic dideoxynucleoside analogues
-
Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by f
- Raghavendra Swamy,Suryakiran,Paradesi Naidu,Venkateswarlu
-
experimental part
p. 191 - 196
(2012/06/30)
-
- Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines
-
A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.
- Matassini, Camilla,Mirabella, Stefania,Goti, Andrea,Cardona, Francesca
-
supporting information; experimental part
p. 3920 - 3924
(2012/09/08)
-
- Tetrabutylammonium tribromide (TBATB): A mild and efficient catalyst for O-isopropylidenation of carbohydrates
-
A wide range of O-isopropylidene derivatives can be prepared from the sugars and their derivatives on reaction with acetone at room temperature by employing 2 mol % of tetrabutylammonium tribromide (TBATB) as a catalyst. Good yields, low catalyst loading, mild reaction conditions, and a non-aqueous workup procedure are some major advantages of this protocol.
- Khan, Abu T.,Khan, Md. Musawwer,Adhikary, Anubendu
-
experimental part
p. 673 - 677
(2011/04/26)
-
- Organoiridium complexes: Efficient catalysts for the formation of sugar acetals and ketals
-
[Cp*IrCl2]2 is used as an efficient promoter for the synthesis of sugar acetals and ketals with good to excellent yields. The catalyst is found to be general for a wide range of sugars.
- Mandal, Soumik,Verma, Prashant Ranjan,Mukhopadhyay, Balaram,Gupta, Parna
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experimental part
p. 2007 - 2010
(2011/12/01)
-
- Highly efficient synthesis of ketoheptoses
-
A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.
- Waschke, Daniel,Thimm, Julian,Thiem, Joachim
-
supporting information; experimental part
p. 3628 - 3631
(2011/09/15)
-
- Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives
-
Enantiomerically pure 3-hydroxypropyl diisopropylidene mannose derivatives were prepared and fully characterized. The procedure is generally applicable to monosaccharides and thus facilitates access to differently substituted glycosidic precursors.
- Kunig, Johannes,L?nnecke, Peter,Hey-Hawkins, Evamarie
-
scheme or table
p. 1154 - 1160
(2011/06/21)
-
- Reactions of several monosaccharide-derived alcohols with p-acetamidobenzenesulfonyl azide and DBU
-
Attempted diazo transfer to 1-O-(2-phenylacetyl)-2,3;5,6-di-O- isopropylidene-α-d-mannofuranose using p-acetamidobenzenesulfonyl azide (p-ABSA) and DBU as base affords 1-O-(2-diazo-2-phenylacetyl)-2,3;5,6-di-O- isopropylidene-α-d-mannofuranose in low yield along with 2,3;5,6-di-O-isopropylidene-α-d-mannofuranose, 1-azido-2,3;5,6-di-O- isopropylidene-β-d-mannofuranose, as well as the unreacted starting material. The azido sugar likely arises from α-mannofuranosyl sulfonate ester formation, through displacement of azide from p-ABSA by the sugar lactol, followed by stereospecific displacement by azide anion on the furanosyl sulfonate ester. This outcome has been studied further with the conditions being applied to several common monosaccharide derivatives. Accessible substrates afford the azido sugar in an overall one-pot alcohol-to-azide conversion, while hindered substrates yield the sulfonate esters.
- Sacui, Iulia A.,Norris, Peter
-
supporting information; experimental part
p. 2670 - 2672
(2011/06/10)
-
- Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents
-
Furanosyl and pyranosyl chlorides react with aryllithium derivatives, obtained by directed ortho-lithiation of activated arenes, to give C-1 aryl glycals in moderate yields.
- Goemez, Ana M.,Casillas, Marta,Rodriguez, Benjamin,Valverde, Serafin,Loepez, J. Cristoebal
-
scheme or table
p. 288 - 302
(2010/08/07)
-
- Design, synthesis, and binding of homologated truncated 4′-thioadenosine derivatives at the human A3 adenosine receptors
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We synthesized homologated truncated 4′-thioadenosine analogues 3 in which a methylene (CH2) group was inserted in place of the glycosidic bond of a potent and selective A3 adenosine receptor antagonist 2. The analogues were designed
- Lee, Hyuk Woo,Kim, Hea Ok,Choi, Won Jun,Choi, Sun,Lee, Jin Hee,Park, Seul-Gi,Yoo, Lena,Jacobson, Kenneth A.,Jeong, Lak Shin
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scheme or table
p. 7015 - 7021
(2010/10/21)
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- A simple and convenient synthetic protocol for O-isopropylidenation of sugars using bromodimethylsulfonium bromide (BDMS) as a catalyst
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Various O-isopropylidene derivatives of sugars and acyclic sugars were obtained in very good yields on reaction with acetone at room temperature with a catalytic amount of bromodimethylsulfonium bromide (BDMS). These O-isopropylidene derivatives can also be prepared in good yields on reaction with 2,2-dimethoxypropane (DMP) in acetonitrile using the same catalyst in shorter reaction times. Some of the advantages of this method are high effectiveness, a nonaqueous workup procedure, economic viability, and good yields.
- Khan, Abu T.,Musawwer Khan
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experimental part
p. 154 - 159
(2011/03/19)
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- A nonself sugar mimic of the HIV glycan shield shows enhanced antigenicity
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Antibody 2G12 uniquely neutralizes a broad range of HIV-1 isolates by binding the high-mannose glycans on the HIV-1 surface glycoprotein, gp120. Antigens that resemble these natural epitopes of 2G12 would be highly desirable components for an HIV-1 vaccine. However, host-produced (self)-carbohydrate motifs have been unsuccessful so far at eliciting 2G12-like antibodies that cross-react with gp120. Based on the surprising observation that 2G12 binds nonproteinaceous monosaccharide D-fructose with higher affinity than D-mannose, we show here that a designed set of nonself, synthetic monosaccharides are potent antigens. When introduced to the terminus of the D1 arm of protein glycans recognized by 2G12, their antigenicity is significantly enhanced. Logical variation of these unnatural sugars pinpointed key modifications, and the molecular basis of this increased antigenicity was elucidated using high-resolution crystallographic analyses. Virus-like particle protein conjugates containing such nonself glycans are bound more tightly by 2G12. As immunogens they elicit higher titers of antibodies than those immunogenic conjugates containing the self D1 glycan motif. These antibodies generated from nonself immunogens also cross-react with this self motif, which is found in the glycan shield, when it is presented in a range of different conjugates and glycans. However, these antibodies did not bind this glycan motif when present on gp120.
- Doores, Katie J.,Fulton, Zara,Hong, Vu,Patel, Mitul K.,Scanlan, Christopher N.,Wormald, Mark R.,Finn,Burton, Dennis R.,Wilson, Ian A.,Davis, Benjamin G.
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scheme or table
p. 17107 - 17112
(2011/02/25)
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- Total syntheses of tubulysins
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The total syntheses of tetrapeptides tubulysins D (1b), U (1c), and V (1d), which are potent tubulin polymerization inhibitors, are described. The synthesis of Tuv (2), an unusual amino acid constituent of tubulysins, includes an 1,3-dipolar cycloaddition
- Shibue, Taku,Hirai, Toshihiro,Okamoto, Iwao,Morita, Nobuyoshi,Masu, Hyuma,Azumaya, Isao,Tamura, Osamu
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supporting information; experimental part
p. 11678 - 11688
(2010/11/18)
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- NEW PHOSPHORUS CONTAINING HETEROCYCLIC COMPOUNDS, SUGAR ANALOGUES, AND COMPOSITIONS HAVING ANTI-CANCER ACTIVITY CONTAINING THE SAME
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The invention provides new anticancer compounds of formula (1) such as defined in the present description. The invention also provides pharmaceutical compositions to be used in human or veterinary medicine, comprising at least one compound of formula (1). The present invention further relates to a compound of formula (1) such as defined in the present description, for use as a drug. The invention further relates to the use of a compound of formula (1) for manufacturing a human or animal anticancer pharmaceutical composition.
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Page/Page column 32-33
(2009/03/07)
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- Synthesis of C-1 alkyl and aryl glycals from pyranosyl or furanosyl chlorides by treatment with organolithium reagents
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Glycosyl chlorides, with ether or isopropylidene acetal protecting groups, readily available from furanoses or pyranoses, can be conveniently transformed into C-1 alkyl or aryl glycals by reaction with alkyl or aryl organolithium reagents.
- Gomez, Ana M.,Pedregosa, Ana,CasiIIas, Marta,Uriel, Clara,Lopez, J. Cristobal
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experimental part
p. 3579 - 3588
(2009/10/26)
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- Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity
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Sirtuins are NAD+ dependent deacetylases that modulate various essential cellular functions. Development of peptide based inhibitors of Sir2s would prove useful both as pharmaceutical agents and as effectors by which downstream cellular alterations can be monitored. Click chemistry that utilizes Huisgen's 1,3-dipolar cycloaddition permits attachment of novel modifications onto the side chain of lysine. Herein, we report the synthesis of peptide analogues prepared using click reactions on Nε-propargyloxycarbonyl protected lysine residues and their characterization as inhibitors of Plasmodium falciparum Sir2 activity. The peptide based inhibitors exhibited parabolic competitive inhibition with respect to acetylated-peptide substrate and parabolic non-competitive inhibition with NAD+ supporting the formation of EI2 and E·NAD+·I2 complexes. Cross-competition inhibition analysis with the non-competitive inhibitor nicotinamide (NAM) ruled out the possibility of the NAM-binding site being the second inhibitor binding site, suggesting the presence of a unique alternate pocket accommodating the inhibitor. One of these compounds was also found to be a potent inhibitor of the intraerythrocytic growth of P. falciparum with 50% inhibitory concentration in the micromolar range.
- Chakrabarty, Subhra Prakash,Ramapanicker, Ramesh,Mishra, Roli,Chandrasekaran, Srinivasan,Balaram, Hemalatha
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scheme or table
p. 8060 - 8072
(2010/03/24)
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- An approach to an enantioselective synthesis of crisamicin A via a novel double Hauser-Kraus annulation strategy
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A double Hauser-Kraus annulation between biscyanophthalide 4 and the d-mannose derived enone 39 provides access to an advanced intermediate 54 that is an excellent scaffold to effect an enantioselective total synthesis of crisamicin A 1.
- Andrey, Olivier,Sperry, Jonathan,Larsen, Uffe S.,Brimble, Margaret A.
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p. 3912 - 3927
(2008/09/20)
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- Amino acid derivatives, v [1]: Synthesis and antiviral evaluation of α-amino acid esters bearing an α-d-mannofuranoside side chain
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D-Mannose was treated with dry acetone in the presence of conc. H 2SO4 to afford 2,3:5,6-di-O-isopropylidene-α-d- mannofuranoside. Treating the latter with ethyl chloroacetate gave carboethoxymethyl 2,3:5,6-di-O-isopropylidene-α-d-mannofuranoside, which was hydrolyzed with N2H4 ? H2O to afford the acid hydrazide derivative. Treating of the acid hydrazide with acylated amino acides, via the azide-coupling method afforded the corresponding O-glycopeptides. Reaction of the glycopeptide methyl esters with N 2H4 ? H2O afforded the corresponding hydrazides, which were coupled with the amino acid methyl esters to afford the dipeptides. Deprotection was carried out by using 70% AcOH. The prepared O-glycopeptides were tested for antiviral activity against hepatitis B virus and showed moderate activities.
- Ali, Omar M.,Abdel-Rahman, Adel A.-H.
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