Isotactic polyethylenimines induce formation of L-amino acids in transamination

被引:34
作者
Bandyopadhyay, Subhajit [1 ]
Zhou, Wenjun [1 ]
Breslow, Ronald [1 ]
机构
[1] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/ol0630604
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Isotactic polyethylenimines with (S)-benzyl side chains were synthesized from 4-(S)-4-benzyl-2-oxazolines. When alpha-keto acids were subjected to transamination in the presence of this polymer, and a pyridoxamine coenzyme modified with hydrophobic chains, enantioselectivity toward the natural isomer (L > D) was observed, followed by racemization of the amino acid products. However, the racemization did not occur when the coenzyme was covalently attached to the polymer.
引用
收藏
页码:1009 / 1012
页数:4
相关论文
共 22 条
[1]   Mimicking enzymatic transaminations:: attempts to understand and develop a catalytic asymmetric approach to chiral α-amino acids [J].
Bachmann, S ;
Knudsen, KR ;
Jorgensen, KA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (14) :2044-2049
[2]  
Breslow R, 2005, ARTIFICIAL ENZYMES, P1, DOI 10.1002/3527606645
[3]   Water exclusion and enantioselectivity in catalysis [J].
Breslow, Ronald ;
Bandyopadhyay, Subhajit ;
Levine, Mindy ;
Zhou, Wenjun .
CHEMBIOCHEM, 2006, 7 (10) :1491-1496
[4]  
BRUICE TC, 1966, BIOORG MECH, V2, pCH8
[5]   Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics [J].
Chruma, JJ ;
Liu, L ;
Zhou, WJ ;
Breslow, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (20) :5873-5883
[6]  
CHUARD T, 1993, CHIMIA, V47, P215
[7]   ANTIBODY-CATALYZED BIMOLECULAR IMINE FORMATION [J].
COCHRAN, AG ;
PHAM, T ;
SUGASAWARA, R ;
SCHULTZ, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6670-6672
[8]   COENZYME AMINO-ACID CHIMERAS - NEW RESIDUES FOR THE ASSEMBLY OF FUNCTIONAL PROTEINS [J].
IMPERIALI, B ;
ROY, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12083-12084
[9]   SYNTHESIS OF A NONIONIC POLYMER SURFACTANT FROM CYCLIC IMINO ETHERS BY THE INITIATOR METHOD [J].
KOBAYASHI, S ;
IIJIMA, S ;
IGARASHI, T ;
SAEGUSA, T .
MACROMOLECULES, 1987, 20 (08) :1729-1734
[10]   Enantioselective reductive amination of alpha-keto acids to alpha-amino acids by a pyridoxamine cofactor in a protein cavity [J].
Kuang, H ;
Brown, ML ;
Davies, RR ;
Young, EC ;
Distefano, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (44) :10702-10706