- Neoglycoprotein cancer vaccines: Synthesis of an azido derivative of GM3 and its efficient coupling to proteins through a new linker
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A GM3 derivative having an azido group on its reducing end was synthesized in nine separate steps, and it was then conjugated to proteins by a new linker. Therefore, the azido group was reduced to a free amino group, which was followed by the introduction
- Xue, Jie,Pan, Yanbin,Guo, Zhongwu
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- Facile and robust methods for the regioselective acylation of: N -acetylneuraminic acid
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The stereoselective synthesis of sialic acid glycoconjugates is still a challenge in the field. Surprisingly, little is known on the regioselective O-substitution of sialic acids. Consequently, the effect of O-protecting groups and/or regioselectively pro
- Shadrick, Melanie,Yu, Charlene,Geringer, Scott,Ritter, Sean,Behm, Alexanndra,Cox, Abby,Lohman, Matt,De Meo, Cristina
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Read Online
- 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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- Facile anomer-oriented syntheses of 4-methylumbelliferyl sialic acid glycosides
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As part of a program to find new sialidases and determine their enzymatic specificity and catalytic activity, a library of 4-methylumbelliferyl sialic acid glycosides derivatised at the C-5 position were prepared fromN-acetylneuraminic acid. Both α- and β-4-methylumbelliferyl sialic acid glycosides were prepared in high yields and stereoselectivity. α-Anomers were accessedviareagent control by utilising additive CH3CN and TBAI, whereas the β-anomers were synthesised through a diastereoselective addition reaction of iodine and the aglycone to the corresponding glycal followed by reduction of the resulting 3-iodo compounds. Both anomer-oriented synthetic pathways allow for gram-scale stereoselective syntheses of the desired C-5 modified neuraminic acid derivatives for use as tools to quantify the enzymatic activity and substrate specificity of known sialidases, and potential detection and investigation of novel sialidases.
- Hassan, Abdullah A.,Oscarson, Stefan
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supporting information
p. 6644 - 6649
(2021/08/10)
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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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- Chemical Synthesis and Enzymatic Testing of CMP-Sialic Acid Derivatives
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The cycloSal approach has been used in the past for the synthesis of a range of phosphorylated bioconjugates. In those reports, cycloSal nucleotides were allowed to react with different phosphate nucleophiles. With glycopyranosyl phosphates as nucleophile
- Wolf, Saskia,Warnecke, Svenja,Ehrit, Joerg,Freiberger, Friedrich,Gerardy-Schahn, Rita,Meier, Chris
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p. 2605 - 2615
(2013/01/16)
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- Exploring the effect of sialic acid orientation on ligand-receptor interactions
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Here, we present the synthesis of two sialo-micelles to validate the significance of sialic acid orientation during specific carbohydrate-protein and carbohydrate-carbohydrate interactions. Our data clearly suggest that orientation of carboxylic acid and
- Yadav, Rohan,Kikkeri, Raghavendra
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scheme or table
p. 7265 - 7267
(2012/08/28)
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- The total synthesis of a ganglioside Hp-s1 analogue possessing neuritogenic activity by chemoselective activation glycosylation
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The total synthesis of ganglioside 2, an analogue of the ganglioside Hp-s1 (1) which displays neuritogenic activity toward the rat pheochromocytoma cell line PC-12 cell in the presence of nerve growth factor (NGF) with an effect (34.0%) greater than that
- Tsai, Yow-Fu,Shih, Cheng-Hua,Su, Yu-Ting,Yao, Chun-Hsu,Lian, Jang-Feng,Liao, Chun-Chen,Hsia, Ching-Wu,Shui, Hao-Ai,Rani, Rashmi
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supporting information; experimental part
p. 931 - 934
(2012/04/04)
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- N,N-Diacetylsialyl chloride-a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter
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N,N-Diacetylneuraminic acid glycosyl chloride was prepared for the first time and made to react with various nucleophiles to give the corresponding α-glycosyl phosphate, β-glycosyl dibenzyl phosphate, α-glycosyl azide, α-phenyl thioglycoside and α-glycosyl xanthate in 65-82% yields and high stereoselectivity while its reactions with simple alcohols were not stereoselective. The new sialyl donor made possible the first stereoselective synthesis of sialic acid glycosyl phosphate with α-configuration and highly efficient synthesis of β-configured sialic acid glycosyl dibenzyl phosphate.
- Orlova, Anna V.,Shpirt, Anna M.,Kulikova, Nadezhda Y.,Kononov, Leonid O.
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experimental part
p. 721 - 730
(2010/06/14)
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- Anomeric samarium(III) intermediates of N-acetylneuraminic acid from anomeric 2-pyridylsulfides
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Treatment of the anomeric 2-thiopyridyl derivative of N-acetylneuraminic acid (sialic acid or Neu5Ac) with samarium diiodide in the presence of aldehydes or ketones provides the corresponding C-sialylated derivatives in excellent yields. The efficiency of
- Malapelle, Adeline,Abdallah, Zouleika,Doisneau, Gilles,Beau, Jean-Marie
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scheme or table
p. 1417 - 1424
(2010/10/03)
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- Ganglioside GM3 derivatives with truncated ceramide moiety: Facial synthesis and inhibitory activity against KB cell growth
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An expeditious sialylation reaction with phenylthioglycoside 4 as a sialyl donor and MeSOTf as a promoter was developed. These conditions are very useful for synthesizing ganglioside GM 3 (1), its C8-ceramide analog 2, and 3-deoxy analog 3 of 2 in an efficient manner. The GM 3 analog 2, whose hydrophilicity is increased by shortening the ceramide moiety, exhibits increased growth inhibiton of KB cells. The 3-hydoxy group of ceramide does not influence its activity against KB cells. Copyright Taylor & Francis Group, LLC.
- Kurosu, Michio,Kitagawa, Isao
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p. 427 - 439
(2007/10/03)
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- Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors
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Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl α-thiosialosides having electron donating and withdrawing subs
- Cao,Meunier,Andersson,Letellier,Roy
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p. 2303 - 2312
(2007/10/02)
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- Stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid
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Treatment of methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate (1) severally with thiophenol, phenylmethanethiol, and ethanethiol in the presence of boron trifluoride etherate gave the corresponding 2-thio-β-glycosides 3-5.Treatment of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate (2) severally with thiophenol in the presence of N,N-di-isopropylethylamine, O-ethyl S-potassium dithiocarbonate, and O-ethyl S-potassium thiocarbonate gave the corresponding 2-thio-α-glycosides, 7, 10, and 11, of which 10 was converted into the ethyl 2-thio-α-glycoside 9 on heating with N,N-dimethylformamide-sodium iodide.The phenyl 2-thioglycosides 3 and 7 were converted into the corresponding sulfones.
- Marra, Alberto,Sinay, Pierre
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