Straightforward Entry to S-Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics

被引：11

作者：

Comegna, Daniela ^{[1
]}

de Paola, Ivan ^{[1
]}

Saviano, Michele ^{[2
]}

Del Gatto, Annarita ^{[1
]}

Zaccaro, Laura ^{[1
]}

机构：

[1] CNR, Inst Biostruct & Bioimaging, Naples, Italy

[2] CNR, Inst Crystallog, Bari, Italy

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 03期

关键词：

EFFICIENT; ACTIVATION; FOLDAMERS; SUGARS;

D O I：

10.1021/ol503664t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohydrate acetates in a few steps. Mild basic conditions make the conjugation reaction compatible with Fmoc-iodo-amino acids. To validate the strategy the glycosylated building blocks were used for SPPS and the unprecedented incorporation of a long thio-oligosaccharide to the peptide chain was demonstrated.

引用

页码：640 / 643

页数：4

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