Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation

被引：25

作者：

Alexander, Stewart R. ^{[1
]}

Fairbanks, Antony J. ^{[1
,2
]}

机构：

[1] Univ Canterbury, Dept Chem, Private Bag 4800, Christchurch 8140, New Zealand

[2] Univ Canterbury, Biomol Interact Ctr, Private Bag 4800, Christchurch 8140, New Zealand

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 28期

关键词：

BOVINE SERUM-ALBUMIN; 2-CHLORO-1,3-DIMETHYLIMIDAZOLINIUM CHLORIDE; 2-IMINO-2-METHOXYETHYL; 1-THIOGLYCOSIDES; UNPROTECTED SUGARS; NEOGLYCOPROTEINS; WATER; GLYCOPROTEINS; STRATEGY; PRODRUG; LIVER;

D O I：

10.1039/c6ob01069e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unprotected carbohydrates can be directly converted into cyanomethyl thioglycosides in a completely stereoselective manner by reaction with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and mercaptoacetonitrile in aqueous solution in the presence of triethylamine. Reaction with methoxide provides 2-imino-2-methoxyethyl (IME) thioglycosides, which may be used directly for the glycosylation of surface protein lysine residues.

引用

页码：6679 / 6682

页数：4

共 3 条

[1] One-pot synthesis of per-O-acetylated thioglycosides from unprotected reducing sugars
Agnihotri, G
Tiwari, P
Misra, AK
CARBOHYDRATE RESEARCH, 2005, 340 (07) : 1393 - 1396
[2] Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water
Qiu, Xin
Fairbanks, Antony J.
ORGANIC LETTERS, 2020, 22 (06) : 2490 - 2493
[3] The direct formation of glycosyl thiols from reducing sugars allows one-pot protein glycoconjugation
Bernardes, Goncalo J. L.
Gamblin, David P.
Davis, Benjamin G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) : 4007 - 4011

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