Enantioselective reductive amination of alpha-keto acids to alpha-amino acids by a pyridoxamine cofactor in a protein cavity

被引：66

作者：

Kuang, H ^{[1
]}

Brown, ML ^{[1
]}

Davies, RR ^{[1
]}

Young, EC ^{[1
]}

Distefano, MD ^{[1
]}

机构：

[1] UNIV MINNESOTA,DEPT CHEM,MINNEAPOLIS,MN 55455

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 44期

关键词：

D O I：

10.1021/ja954271z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Adipocyte lipid binding protein (ALBP) is a small 131 residue protein with a simple architecture that consists of two orthogonal planes of beta-sheet secondary structure. This protein binds a variety of fatty acids in a large cavity formed between the two sheets such that the bound ligands are completely enclosed within the protein. In this paper, the synthesis of an ALBP conjugate (ALBP-PX) containing a pyridoxamine cofactor attached to a thiol within the protein interior is described. The conjugate was characterized by mass spectrometry, UV/vis spectroscopy, and gel filtration chromatography. ALBP-PX reductively aminates a number of alkyl, aryl, and side chain functionalized alpha-keto acids to alpha-amino acids with enantioselectivities as high as 94% ee.

引用

页码：10702 / 10706

页数：5

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