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.
引用
收藏
页码：2582 / 2585
页数：4
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