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
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页码：10241 / 10252
页数：12
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