仿生不对称转氨化合成手性α,ω-二氨基酸  

Synthesis of Chiral α,ω-Diamino Acids via Asymmetric Biomimetic Transamination

作　　者：陈剑锋 侯承康[2] 许东芳 梁撼宇[2] 袁伟成 赵宝国[2] CHEN Jian-feng;HOU Cheng-kang;XU Dong-fang;LIANG Han-yu;YUAN Wei-cheng;ZHAO Bao-guo(Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratoryof Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234, China;University of Chinese Academy of Sciences, Beijing 100049, China)

机构地区：[1]中国科学院成都有机化学研究所,四川成都610041 [2]上海师范大学资源化学教育部重点实验室和上海市稀土功能材料重点实验室,上海200234 [3]中国科学院大学,北京100049

出　　处：《合成化学》2019年第9期680-688,697,共10页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21672148,21871181)

摘　　要：以ω-溴-α-酮酸为原料,发展了一种合成手性α,ω-二氨基酸的高效方法,通过手性吡哆胺催化ω-溴-α-酮酸的不对称转氨化和NH 3 对ω-溴的取代反应,在温和条件下一锅法合成了6个带有不同长度直链手性α,ω-二氨基酸,收率49~93%, ee 值最高可以达91%,其结构经 1 H NMR和 13 C NMR表征。A two-step one-pot process for the synthesis of chiral lipidic α,ω-diamino acids has been developed. Chiral pyridoxamine-catalyzed asymmetric transamination of ω-bromo α-keto acids, followed by substitution of the ω-bromide with NH 3 , afforded six chiral α,ω-diamino acids in 49%~93% yields with up to 91% ee under very mild conditions. The structures were characterized by 1 H NMR and 13 C NMR.

关 键 词：ω-溴-α-酮酸 手性吡哆胺 仿生催化 仿生不对称转氨化 维生素B 6 α ω-二氨基酸 

分 类 号：O623.7[理学—有机化学]