1,2-反式-2-乙酰氨基-2-去氧同型亚氨基糖的合成。

Synthesis of 1,2-trans-2-acetamido-2-deoxyhomoiminosugars.

机构信息

Glycochemistry Group of "Organic Synthesis" Team, Université de Poitiers , UMR-CNRS 7285 IC2MP, Bât. B28, 4 rue Michel Brunet, TSA 51106, 86073 Poitiers Cedex 9, France.

出版信息

Org Lett. 2014 Nov 7;16(21):5516-9. doi: 10.1021/ol502929h. Epub 2014 Oct 20.

DOI:10.1021/ol502929h

PMID:25330462

Abstract

The first synthesis of 1,2-trans-homoiminosugars devised as mimics of β-D-GlcNAc and α-D-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a β-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The β-D-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.

摘要

首次设计了 1,2-反式同型亚氨基糖作为β-D-GlcNAc 和 α-D-ManNAc 的类似物进行合成。关键步骤包括环状亚磺酸盐的区域选择性叠氮化和应用于多羟基氮杂环庚烷的β-氨基醇骨架重排。β-D-GlcNAc 衍生物已与丝氨酸偶联，得到亚氨基糖 C-氨基酸。这两个同型亚氨基糖表现出中等的糖苷酶抑制作用。