Simple and Efficient Preparation of O- and S-GIcNAcylated Amino Acids through InBr3-Catalyzed Synthesis of β-N-Acetylglycosides from Commercially Available Reagents

被引：18

作者：

De Leon, Cesar A. ^{[1
]}

Lang, Geoffrey ^{[1
]}

Saavedra, Marcos I. ^{[1
]}

Pratt, Matthew R. ^{[1
,2
]}

机构：

[1] Univ Southern Calif, Dept Chem, Los Angeles, CA 90089 USA

[2] Univ Southern Calif, Dept Mol & Computat Biol, Los Angeles, CA 90089 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 16期

基金：

美国国家卫生研究院;

关键词：

GLCNAC; GLUCOSAMINE; GLYCOSYLATION; DERIVATIVES; PEPTIDE; BIOLOGY; DONORS;

D O I：

10.1021/acs.orglett.8b02182

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The facile synthesis of serine, threonine, and cysteine beta-glycosides using commercially available peracetylated beta-N-acetylglucosamine (beta-Ac(4)GlcNAc) and catalytic amounts of indium bromide (InBr3) is described. This method involves only inexpensive reagents that require no further modification or special handling. The reagents are simply mixed, dissolved, and refluxed to afford the GlcNAcylated amino acids in great yields (70-80%). This operationally simple procedure should facilitate the study of O-GlcNAcylation without necessitating expertise in synthetic carbohydrate chemistry.

引用

页码：5032 / 5035

页数：4

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