Steric-control for the enantioselective hydrolysis of amino acid esters with membrane-bound enzyme models

被引：15

作者：

Tanoue, O ^{[1
]}

Baba, M ^{[1
]}

Tokunaga, Y ^{[1
]}

Goto, K ^{[1
]}

Matsumoto, Y ^{[1
]}

Ueoka, R ^{[1
]}

机构：

[1] Kumamoto Inst Technol, Grad Course Appl Chem, Kumamoto 8600082, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(99)00129-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The apparently complete stereoselectivity (k(a,obsd)(L)/k(a,obsd)(D) = infinity) for the hydrolysis of enantiomeric substrate (p-nitrophenyl n-dodecanoyl-D(L)-phenyalaninate; C-12-D(L)-Phe-PNP) catalyzed by active tripeptide (N-(benzyloxycarbonyl)-L-phenylalanyl -L-histidyl-L-leucine; Z-PheHisLeu) was attained by regulating the composition of coaggregates, ionic strength, and temperature, in coaggregate systems composed of vesicular and micellar surfactants. This can be related to the optimization of conformation in the Z-PheHisLeu catalyst to react with amino acid esters by changing of physical properties of coaggregates. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2129 / 2132

页数：4

共 5 条

[1] Steric control for the hydrolysis of enantiomeric and diastereomeric esters - A new development of supramolecular assemblies
Goto, K
Ueoka, R
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (09) : 803 - 813
[2] EXPERIMENTAL AND COMPUTER MODELING STUDIES OF MICELLAR DIASTEREOSELECTIVITY
MOSS, RA
HENDRICKSON, TF
UEOKA, R
KIM, KY
WEINER, PK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) : 4363 - 4372
[3] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CLEAVAGE OF AMINO-ACID ESTERS IN COAGGREGATES OF CONTROLLED SIZE
UEOKA, R
MATSUMOTO, Y
YOSHINO, T
HIROSE, T
MOSS, RA
KIM, KY
SWARUP, S
[J]. TETRAHEDRON LETTERS, 1986, 27 (10) : 1183 - 1186
[4] UEOKA R, 1989, CHEM PHARM BULL, V37, P2263
[5] MEMBRANE MATRIX FOR THE HYDROLYSIS OF AMINO-ACID ESTERS WITH MARKED ENANTIOSELECTIVITY
UEOKA, R
MATSUMOTO, Y
MOSS, RA
SWARUP, S
SUGII, A
HARADA, K
KIKUCHI, J
MURAKAMI, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1588 - 1595

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