Rational De Novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

被引：6

作者：

Eguchi, T ^{[1
]}

Fukuda, M ^{[1
]}

Toyooka, Y ^{[1
]}

Kakinuma, K ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 152, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 5-6期

关键词：

NADH mimics; synthesis; asymmetric reduction; semi-empirical calculation;

D O I：

10.1016/S0040-4020(97)10294-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：705 / 714

页数：10

共 52 条

[1] On transition structures for hydride transfer step in enzyme catalysis. A comparative study on models of glutathione reductase derived from semiempirical, HF, and DFT methods
Andres, J
Moliner, V
Safont, VS
Domingo, LR
Picher, MT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) : 7777 - 7783
[2] A THEORETICAL-STUDY OF THE MEYER-SCHUSTER REACTION-MECHANISM - MINIMUM-ENERGY PROFILE AND PROPERTIES OF TRANSITION-STATE STRUCTURE
ANDRES, J
CARDENAS, R
SILLA, E
TAPIA, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (03) : 666 - 674
[3] AN ALGORITHM FOR THE LOCATION OF TRANSITION-STATES
BAKER, J
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1986, 7 (04) : 385 - 395
[4] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
BARTON, DHR
MCCOMBIE, SW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
[5] STUDY OF THE MECHANISM OF THE HYDRIDE TRANSFER WITH A HIGHLY REACTIVE AND STEREOSELECTIVE NADH MODEL
BEDAT, J
PLE, N
DUPAS, G
BOURGUIGNON, J
QUEGUINER, G
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (04) : 923 - 932
[6] NADH MODELS IN THE PYRROLO[3,4-B]PYRIDINE SERIES - ROLE OF THE CYCLIZED STRUCTURE IN THE STEREOCONTROL OF REDUCTIONS
BEDAT, J
LEVACHER, V
DUPAS, G
QUEGUINER, G
BOURGUIGNON, J
[J]. CHEMISTRY LETTERS, 1995, (04) : 327 - 328
[7] BERKOUS R, 1994, B SOC CHIM FR, V131, P632
[8] NADH MIMICS FOR THE STEREOSELECTIVE REDUCTION OF BENZOYLFORMATES TO THE CORRESPONDING MANDELATES
BURGESS, VA
DAVIES, SG
SKERLJ, RT
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (05) : 299 - 328
[9] CHIRAL ORGANOMETALLIC NADH MIMICS - HIGHLY STEREOSELECTIVE REDUCTIONS OF ETHYL BENZOYLFORMATE WITH A 1,4-DIHYDRONICOTINOYL FRAGMENT ATTACHED TO THE HOMOCHIRAL AUXILIARY [(ETA-5-C5H5)FE(CO)(PPH3)] AND POSSESSING A HOMOCHIRAL BETA-HYDROXY-CARBOXAMIDE AT C-5
BURGESS, VA
DAVIES, SG
SKERLJ, RT
WHITTAKER, M
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (07) : 871 - 901
[10] Burkert U., 1982, Molecular Mechanics

← 1 2 3 4 5 6 →