Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid
Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid
复制标题
DOI：
10.1016/s0040-4039(02)01844-0
复制
发表时间：
2002-10-21
影响因子：
1.8
通讯作者：
Chan, C
中科院分区：
文献类型：
--
作者：
Roberts, JL;Chan, C
meso-2，6-二氨基庚二酸是细菌细胞壁的重要连接组分，也是L-赖氨酸的生物合成前体，已经以立体特异性方式与L-天冬氨酸和L-谷氨酸进行了差异保护。建立第二手性中心的关键步骤涉及丙酮酸部分与Alpine-Borane（R）的不对称还原。S-2-氨基-6-氧代庚二酸是四氢吡啶二甲酸的水解开链形式，是内消旋-2，6-二氨基庚二酸的生物合成前体，也通过关键丙酮酸中间体的脱保护制备。(C)2002爱思唯尔科技有限公司。保留所有权利。
meso-2,6-Diaminopimelic acid, an important linking component of bacterial cell walls and a biosynthetic precursor of L-lysine has been prepared differentially protected in a stereospecific manner from both L-aspartic and L-glutamic acid. The key step to establish the second chiral center involves the asymmetric reduction of a pyruvate moiety with Alpine-Borane(R). S-2-Amino-6-oxopimelic acid, the hydrolyzed open chain form of tetrahydrodipicolinic acid, a biosynthetic precursor of meso-2,6-diaminopimelic acid, was also prepared via deprotection of the key pyruvate intermediate. (C) 2002 Elsevier Science Ltd. All rights reserved.