SYNTHESIS OF A KEY INTERMEDIATE IN THE DIAMINOPIMELATE PATHWAY TO L-LYSINE - 2,3,4,5-TETRAHYDRODIPICOLINIC ACID

被引：28

作者：

CHRYSTAL, EJT

COUPER, L

ROBINS, DJ

机构：

[1] UNIV GLASGOW,DEPT CHEM,GLASGOW G12 8QQ,LANARK,SCOTLAND

[2] ZENECA AGROCHEM,JEALOTTS HILL RES STN,BRACKNELL RG12 6EY,BERKS,ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 37期

关键词：

D O I：

10.1016/0040-4020(95)00618-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,3,4,5-Tetrahydrodipicolinic acid (3) is a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7). It was synthesized as the stable racemic potassium salt (25) from dipicolinic acid (14) by esterification, hydrogenation to the cis-diester (17), followed by elimination of p-toluenesuifinic acid from the N-toluenesulfonyl derivative (24) of dimethyl cis-piperidine-2,6-dicarboxylate with concomitant cleavage of the ester groups. (+/-)-2,3,4,5-Tetrahydrodipicolinic acid is unstable in neutral or acidic solution, and in basic solution it exists in equilibrium with the corresponding enamine (27) and 2-oxo-6-aminoadipate (26).

引用

页码：10241 / 10252

页数：12

共 24 条

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