Comparison of microbiologically and enzymatically mediated Baeyer-Villiger oxidations: Synthesis of optically active caprolactones

被引：37

作者：

Alphand, V

Furstoss, R

PedragosaMoreau, S

Roberts, SM

Willetts, AJ

机构：

[1] FAC SCI LUMINY,GRP CHIM ORGAN & BIOORGAN,URA CNRS 1320,F-13288 MARSEILLE 9,FRANCE

[2] UNIV EXETER,DEPT CHEM,EXETER EX4 4QD,DEVON,ENGLAND

[3] UNIV EXETER,DEPT BIOL SCI,EXETER EX4 4QD,DEVON,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 15期

关键词：

D O I：

10.1039/p19960001867

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active a-substituted caprolactones (7-substituted oxepan-2-ones) were obtained by biocatalysed Baeyer-Villiger oxidations of various a-substituted cyclohexanones using either whole-cells of Acinetobacter TD63 or a purified cyclohexanone monooxygenase from Ps. putida NCIMB 10007(MO2). A refinement of the previously established active site model is proposed.

引用

页码：1867 / 1872

页数：6

共 36 条

[11] OPTICALLY-ACTIVE LACTONES FROM A BAEYER-VILLIGER-TYPE METAL-CATALYZED OXIDATION WITH MOLECULAR-OXYGEN
BOLM, C
SCHLINGLOFF, G
WEICKHARDT, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18): : 1848 - 1849
[12] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
CHEN, CS
FUJIMOTO, Y
GIRDAUKAS, G
SIH, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
[13] METABOLISM OF TRANS-CYCLOHEXAN-1,2-DIOL BY AN ACINETOBACTER SPECIES
DAVEY, JF
TRUDGILL, PW
[J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1977, 74 (01): : 115 - 127
[14] RESOLUTION OF RACEMIC EPSILON-LACTONES
FELLOUS, R
LIZZANICUVELIER, L
LOISEAU, MA
SASSY, E
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (03) : 343 - 346
[15] OXIDATION OF SOME PROCHIRAL 3-SUBSTITUTED CYCLOBUTANONES USING MONOOXYGENASE ENZYMES - A SINGLE-STEP METHOD FOR THE SYNTHESIS OF OPTICALLY ENRICHED 3-SUBSTITUTED GAMMA-LACTONES
GAGNON, R
GROGAN, G
GROUSSAIN, E
PEDRAGOSAMOREAU, S
RICHARDSON, PF
ROBERTS, SM
WILLETTS, AJ
ALPHAND, V
LEBRETON, J
FURSTOSS, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (20): : 2527 - 2528
[16] BIOLOGICAL BAEYER-VILLIGER OXIDATION OF SOME MONOCYCLIC AND BICYCLIC KETONES USING MONOOXYGENASES FROM ACINETOBACTER-CALCOACETICUS NCIMB-9871 AND PSEUDOMONAS-PUTIDA NCIMB-10007
GAGNON, R
GROGAN, G
LEVITT, MS
ROBERTS, SM
WAN, PWH
WILLETTS, AJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18): : 2537 - 2543
[17] BIOTRANSFORMATION OF CYCLOALKENONES - CONTROLLED OXIDATIVE AND REDUCTIVE BIOCONVERSIONS BY PSEUDOMONAS-PUTIDA
GROGAN, G
ROBERTS, S
WAN, P
WILLETTS, A
[J]. BIOTECHNOLOGY LETTERS, 1994, 16 (11) : 1173 - 1178
[18] CAMPHOR-GROWN PSEUDOMONAS-PUTIDA, A MULTIFUNCTIONAL BIOCATALYST FOR UNDERTAKING BAEYER-VILLIGER MONOOXYGENASE-DEPENDENT BIOTRANSFORMATIONS
GROGAN, G
ROBERTS, S
WAN, P
WILLETTS, A
[J]. BIOTECHNOLOGY LETTERS, 1993, 15 (09) : 913 - 918
[19] PLATINUM-CATALYZED OXIDATIONS WITH HYDROGEN-PEROXIDE - ENANTIOSPECIFIC BAEYER-VILLIGER OXIDATION OF CYCLIC-KETONES
GUSSO, A
BACCIN, C
PINNA, F
STRUKUL, G
[J]. ORGANOMETALLICS, 1994, 13 (09) : 3442 - 3451
[20] DIKETOCAMPHANE ENANTIOMER-SPECIFIC BAEYER-VILLIGER MONOOXYGENASES FROM CAMPHOR-GROWN PSEUDOMONAS-PUTIDA ATCC-17453
JONES, KH
SMITH, RT
TRUDGILL, PW
[J]. JOURNAL OF GENERAL MICROBIOLOGY, 1993, 139 : 797 - 805

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