BIOTRANSFORMATION OF ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS - SULFIDES, SULFOXIDES, SULFONES, NITRILES AND ESTERS BY YEAST SPECIES - CARBONYL GROUP AND CARBON-CARBON DOUBLE-BOND REDUCTION

被引：38

作者：

KOUL, S ^{[1
]}

CROUT, DHG ^{[1
]}

ERRINGTON, W ^{[1
]}

TAX, J ^{[1
]}

机构：

[1] UNIV WARWICK,DEPT CHEM,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 23期

关键词：

D O I：

10.1039/p19950002969

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of alpha beta-unsaturated ketones with gamma-sulfide, sulfoxide, sulfone, nitrile and ester functions has been investigated. Both C=O and C=C reduction was observed. In the sulfur series, C=O bond reduction was always observed, but significant C=C bond reduction was observed only with the sulfide. The unsaturated nitriles gave the corresponding alcohol as the major bioreduction product, with smaller but significant amounts of fully reduced product. A similar result was obtained with the ester substrate. Relative and absolute configurations of bioreduction products were determined, A comparison was made between reductions catalysed by bakers' yeast (Saccharomyces cerevisiae) and by other yeasts (Zygosaccharomyces rouxii, Pichia capsulata, P. farinosa, Candida chalmersi and C. diddensiae). The tendency of Z. rouxii to give products enantiomeric with those obtained using S. cerevisiae was noted. The relationship between substrate structure and the stereochemistry of C=C double bond reduction is discussed.

引用

页码：2969 / 2988

页数：20

共 70 条

[51] ASYMMETRIC HYDROGENATION OF 2-ARYL-1-NITROPROPENES BY FERMENTING BAKERS-YEAST [J].

OHTA, H ;

OZAKI, K ;

TSUCHIHASHI, G .

CHEMISTRY LETTERS, 1987, (01) :191-192

[52]

POLITO AJ, 1971, J BIOL CHEM, V246, P4178

[53] ASYMMETRIC REDUCTION OF CARBON-CARBON DOUBLE-BONDS OF CONJUGATED ENONES WITH FERMENTING BAKERS-YEAST [J].

SAKAI, T ;

MATSUMOTO, S ;

HIDAKA, S ;

IMAJO, N ;

TSUBOI, S ;

UTAKA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (11) :3473-3475

[54] DIASTEREOSELECTIVE ALPHA-ALKYLATION OF BETA-HYDROXY SULFOXIDES AND ITS APPLICATION TO THE SYNTHESIS OF (+)-DISPARLURE AND (-)-DISPARLURE [J].

SATO, T ;

ITOH, T ;

FUJISAWA, T .

TETRAHEDRON LETTERS, 1987, 28 (46) :5677-5680

[55] (S)-BETA,OMEGA-DIHYDROXYALKYL PHENYL SULFONES - SYNTHESIS BY BAKERS-YEAST REDUCTION AND USE AS PRECURSORS OF OPTICALLY-ACTIVE LACTONES [J].

SATO, T ;

OKUMURA, Y ;

ITAI, J ;

FUJISAWA, T .

CHEMISTRY LETTERS, 1988, (09) :1537-1540

[56] PREPARATION OF CHIRAL-C5-BUILDING BLOCKS FOR TERPENE SYNTHESIS BY BAKERS-YEAST REDUCTION OF SULFUR-FUNCTIONALIZED PRENYL DERIVATIVES [J].

SATO, T ;

HANAYAMA, K ;

FUJISAWA, T .

TETRAHEDRON LETTERS, 1988, 29 (18) :2197-2200

[57]

SERVI S, 1990, SYNTHESIS-STUTTGART, P1

[58]

SHELDRICK GM, 1990, SHELXTL PLUS

[59]

SHELDRICK GM, 1994, SHELXL 93 PROGRAM CR

[60] STEREOCHEMICAL CONTROL OF YEAST REDUCTIONS .5. CHARACTERIZATION OF THE OXIDOREDUCTASES INVOLVED IN THE REDUCTION OF BETA-KETO-ESTERS [J].

SHIEH, WR ;

GOPALAN, AS ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (10) :2993-2994

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