通过有机催化模拟利用磷酸二羟基丙酮的醛缩酶：一条通往碳水化合物和氨基糖的简便途径。

Mimicking dihydroxy acetone phosphate-utilizing aldolases through organocatalysis: a facile route to carbohydrates and aminosugars.

作者信息

Suri Jeff T, Ramachary Dhevalapally B, Barbas Carlos F

机构信息

The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

出版信息

Org Lett. 2005 Mar 31;7(7):1383-5. doi: 10.1021/ol0502533.

DOI:10.1021/ol0502533

PMID:15787512

Abstract

[reaction: see text] A practical and environmentally friendly organocatalytic strategy designed to mimic the DHAP aldolases has been developed and shown to be effective in the preparation of carbohydrates and aminosugars. (S)-Proline and (S)-2-pyrrolidine-tetrazole catalyzed the aldol reaction between dihydroxy acetone variants such as 1,3-dioxan-5-one and 2,2-dimethyl-1,3-dioxan-5-one with aldehydes to give the corresponding polyols in good yields with very high ees.

摘要

[反应：见正文] 一种旨在模拟二羟基丙酮醛缩酶的实用且环保的有机催化策略已被开发出来，并证明在制备碳水化合物和氨基糖方面是有效的。（S）-脯氨酸和（S）-2-吡咯烷四唑催化二羟基丙酮变体（如1,3-二氧六环-5-酮和2,2-二甲基-1,3-二氧六环-5-酮）与醛之间的羟醛反应，以高对映体过量率和良好产率得到相应的多元醇。