Process for the enzymatic resolution of N-(alkoxycarbonyl)-4-ketoproline
alkyl esters or N-(alkoxycarbonyl)-4-hydroxyproline alkyl esters using
Candida antarctica lipase B
    40.
    发明授权
    Process for the enzymatic resolution of N-(alkoxycarbonyl)-4-ketoproline alkyl esters or N-(alkoxycarbonyl)-4-hydroxyproline alkyl esters using Candida antarctica lipase B 失效
    使用南极假丝酵母脂肪酶B酶解拆分N-(烷氧基羰基)-4-酮脯氨酸烷基酯或N-(烷氧基羰基)-4-羟基脯氨酸烷基酯的方法

    公开(公告)号:US5928933A

    公开(公告)日:1999-07-27

    申请号:US105713

    申请日:1998-06-26

    摘要: The present invention relates to a process for the enzymatic resolution of racemic mixtures of N-(alkoxycarbonyl)-4-keto-D,L-proline alkyl esters, using Candida antarctica lipase fraction B (CALB) as enzyme catalyst to enantioselectively hydrolyze the alkyl ester of one of the two enantiomers present. Separating the unreacted N-(alkoxycarbonyl)-4-keto-D-proline alkyl ester from the N-(alkoxycarbonyl)-4-keto-L-proline, followed by hydrogenation of the keto group of the D-isomer and subsequent hydrolysis of the ester and N-(alkoxy-carbonyl) groups produces cis-4-hydroxy-D-proline in high yield. Diastereomeric mixtures of N-(alkoxycarbonyl)-4-hydroxyproline alkyl esters can also be resolved using CALB to ultimately produce cis-4-hydroxy-D-proline or trans-4-hydroxy-L-proline.

    摘要翻译: 本发明涉及使用南极假丝酵母脂肪酶B(CALB)作为酶催化剂来解离N-(烷氧基羰基)-4-酮基-D-脯氨酸烷基酯的外消旋混合物的方法,以对映体水解烷基 存在两种对映体之一的酯。 从N-(烷氧基羰基)-4-酮-L-脯氨酸分离未反应的N-(烷氧基羰基)-4-酮基-D-脯氨酸烷基酯,然后氢化D-异构体的酮基,随后水解 酯和N-(烷氧基 - 羰基)基团以高产率产生顺式-4-羟基-D-脯氨酸。 N-(烷氧基羰基)-4-羟基脯氨酸烷基酯的非对映异构体混合物也可以使用CALB来分解,以最终产生顺式-4-羟基-D-脯氨酸或反式-4-羟基-L-脯氨酸。