Stereoselective Synthesis of Natural and Non-natural Thomsen-nouveau Antigens and Hydrazide Derivatives

被引：16

作者：

Shaik, Ahmad Ali

Nishat, Sharmeen

Andreana, Peter R. ^{[1
]}

机构：

[1] Univ Toledo, Dept Chem & Biochem, Toledo, OH 43606 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 11期

基金：

美国国家卫生研究院;

关键词：

CARBOHYDRATE ANTIGEN; GOLD NANOPARTICLES; CANCER; TN; VACCINES; DONORS; GLYCOPEPTIDES; DISACCHARIDE; RECOGNITION; SUBSTITUENT;

D O I：

10.1021/acs.orglett.5b00512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to alpha- or beta-anomers in excellent yields (72-96%) and selectivity (similar to 100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.

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收藏

页码：2582 / 2585

页数：4

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