Highly reactive and stereospecific reaction of quinoline-type NADH model compounds with methyl benzoylformate

被引：37

作者：

Mikata, Y ^{[1
]}

Hayashi, K

Mizukami, K

Matsumoto, S

Yano, S

Yamazaki, N

Ohno, A

机构：

[1] Nara Womens Univ, Fac Sci, Dept Chem, Nara 6308506, Japan

[2] Kyoto Univ, Inst Chem Res, Uji 6110011, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 07期

关键词：

NADH model; NAD model; axial chirality; HPLC; optical resolution;

D O I：

10.1016/S0040-4039(99)02227-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NADH model compounds with a dihydroquinoline ring can reduce methyl benzoylformate with very high reactivity and stereospecificity. Chiral column HPLC is effective in the separation and analysis of enantiomers of NADH and NAD model compounds, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：1035 / 1038

页数：4

相关论文

共 11 条

[1] REGIO-SELECTIVE AND STEREO-SELECTIVE HYDRIDE UPTAKE IN MODEL SYSTEMS RELATED TO 3-CARBAMOYL PYRIDINIUM COMPOUNDS [J].

DEKOK, PMT ;

BUCK, HM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (15) :1009-1010

[2] HIGHLY REACTIVE AND STEREOSELECTIVE (R) AND (S)-3-(N,N-DIMETHYLCARBAMOYL)-1,2,4-TRIMETHYL-1,4-DIHYDROPYRIDINES FOR NADH NAD+ MIMICRY [J].

DEKOK, PMT ;

BASTIAANSEN, LAM ;

VANLIER, PM ;

VEKEMANS, JAJM ;

BUCK, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1313-1320

[3] STEREOSELECTIVE HYDRIDE UPTAKE IN MODEL-SYSTEMS RELATED TO THE REDOX-COUPLE NAD+/NADH [J].

DEKOK, PMT ;

DONKERSLOOT, MCA ;

VANLIER, PM ;

MEULENDIJKS, GHWM ;

BASTIAANSEN, LAM ;

VANHOOFF, HJG ;

KANTERS, JA ;

BUCK, HM .

TETRAHEDRON, 1986, 42 (04) :941-959

[4] THE HYDRIDE-DONATION REACTION OF REDUCED NICOTINAMIDE ADENINE-DINUCLEOTIDE .2. MINDO-3 AND STO-3G CALCULATIONS ON THE ROLE OF THE CONH2 GROUP IN ENZYMATIC-REACTIONS [J].

DONKERSLOOT, MCA ;

BUCK, HM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (22) :6554-6558

[5] A MECHANISTIC BASIS FOR THE STEREOSELECTIVITY OF ENZYMATIC TRANSFER OF HYDROGEN FROM NICOTINAMIDE COFACTORS [J].

NAMBIAR, KP ;

STAUFFER, DM ;

KOLODZIEJ, PA ;

BENNER, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5886-5890

[6]

OHNO A, 1979, J AM CHEM SOC, V101, P7036, DOI 10.1021/ja00517a043

[7] NAD(P)+-NAD(P)H MODELS .57. STEREOCHEMISTRY IN (NET) HYDRIDE TRANSFER FROM AND TO NAD(P)+-NAD(P)H MODELS - CHIRALITY SINK [J].

OHNO, A ;

KASHIWAGI, M ;

ISHIHARA, Y ;

USHIDA, S ;

OKA, S .

TETRAHEDRON, 1986, 42 (04) :961-973

[8] NAD(P)+-NAD(P)H models.: 88. Stereoselection without steric effect but controlled by electronic effect of a carbonyl group:: Syn/Anti reactivity ratio, kinetic isotope effect, and an electron-transfer complex as a reaction intermediate [J].

Ohno, A ;

Ishikawa, Y ;

Yamazaki, N ;

Okamura, M ;

Kawai, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (06) :1186-1192

[9] NAD(P)+-NAD(P)H MODELS .61. AN INTERCONVERSION BETWEEN CENTRAL AND AXIAL CHIRALITIES AS AN EVIDENCE FOR A FUNCTIONAL-MODEL OF CHEMICAL EVOLUTION OF AN ENZYME [J].

OHNO, A ;

OHARA, M ;

OKA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6438-6440

[10] NAD(P)H-NAD(P)+ MODELS .73. STRUCTURE-STEREOCHEMISTRY RELATIONSHIP IN THE REACTION OF NAD ANALOG [J].

OHNO, A ;

MIKATA, Y ;

GOTO, M ;

KASHIWAGI, T ;

TANAKA, T ;

SAWADA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (01) :81-86