通过酶促氨解使3-(苄基氨基)戊二酸二甲酯去对称化合成(R)-3,4-二氨基丁酸

Synthesis of (R)-3,4-diaminobutanoic acid by desymmetrization of dimethyl 3-(benzylamino)glutarate through enzymatic ammonolysis.

作者信息

López-García Mónica, Alfonso Igancio, Gotor Vicente

机构信息

Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, Spain.

出版信息

J Org Chem. 2003 Jan 24;68(2):648-51. doi: 10.1021/jo026254f.

DOI:10.1021/jo026254f

PMID:12530904

Abstract

Lipase B from Candida antarctica is shown to be a highly efficient catalyst for the desymmetrization of dimethyl 3-(benzylamino)glutarate (1) through aminolysis and ammonolysis reactions. Using this procedure, enantiopure monoamides are obtained in high yield. The synthetic value of these compounds is demonstrated by the preparation of an enantiopure nonnatural amino acid, i.e. (R)-3,4-diaminobutanoic acid [(+)-12].

摘要

南极假丝酵母脂肪酶B被证明是一种高效催化剂，可通过氨解和氨化反应使3-(苄基氨基)戊二酸二甲酯(1)去对称化。采用该方法可高产率获得对映体纯的单酰胺。通过制备对映体纯的非天然氨基酸，即(R)-3,4-二氨基丁酸[(+)-12]，证明了这些化合物的合成价值。