Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination
Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination
复制标题
受酶启发的轴向手性吡哆胺配备协同侧胺链，用于对映选择性仿生转氨
DOI：
10.1021/jacs.6b03930
复制
发表时间：
2016-08-31
影响因子：
15
通讯作者：
Zhao, Baoguo
中科院分区：
文献类型：
--
作者：
Liu, Yong Ethan;Lu, Zhaole;Zhao, Baoguo
酶促转氨作用由吡哆醛/吡哆胺催化，并且涉及转氨酶中赖氨酸残基的显着协同催化。受转氨酶的启发，我们开发了一类带有侧胺臂的轴向手性吡哆胺 11。吡哆胺在α-酮酸的不对称氨基转移中表现出高催化活性和优异的对映选择性，以67-99%的收率得到各种α-氨基酸，其中ee's为83-94%。侧胺臂可能像赖氨酸残基在生物转氨作用中一样参与协同催化，并且在活性和对映选择性方面对转氨作用具有重要影响。
Enzymatic transamination is catalyzed by pyridoxal/pyridoxamine, and it involves remarkable cooperative catalysis of a Lys residue in the transaminase. Inspired by transaminases, we developed a, class of axially chiral pyridoxamines 11 bearing a lateral amine arm. The pyridoxamines exhibited high catalytic activity and excellent enantioselectivity in asymmetric transamination of alpha-keto acids, to give various alpha-amino acids in 67-99% yields with.83-94% ee's. The lateral amine arm likely participates in cooperative catalysis as the Lys residue does in biological transamination and has an important impact on the transamination in terms of activity and enantioselectivity.