Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination

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 cat...

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Published inJournal of the American Chemical Society Vol. 138; no. 34; pp. 10730 - 10733
Main Authors Liu, Yong Ethan, Lu, Zhaole, Li, Bo, Tian, Jiaxin, Liu, Feng, Zhao, Junyu, Hou, Chengkang, Li, Yingkun, Niu, Lili, Zhao, Baoguo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.08.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
PROTEIN CAVITY
ASPARTATE-AMINOTRANSFERASE
ALPHA-KETO ESTERS
EFFICIENT SYNTHESIS
LYSINE RESIDUE
SHIFT REACTION
CATALYTIC ASYMMETRIC-SYNTHESIS
COVALENT CATALYSIS
REDUCTIVE AMINATION
AQUEOUS SYSTEMS
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Summary: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 α-keto acids, to give various α-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.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b03930