Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases

被引:155
作者
Alphand, V
Carrea, G
Wohlgemuth, R
Furstoss, R
Woodley, JM
机构
[1] UCL, Dept Biochem Engn, London WC1E 7JE, England
[2] Fluka AG, Dept Biochem, CH-9470 Buchs, Switzerland
[3] CNR, Inst Chim Riconoscimento Mol, I-20131 Milan, Italy
[4] CNRS, Grp Biocatalyse & Chim Fine, F-13288 Marseille, France
关键词
D O I
10.1016/S0167-7799(03)00144-6
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Biocatalysis is coming of age, with an increasing number of reactions being scaled-up and developed. The diversity of reactions is also increasing and oxidation reactions have recently been considered for scale-up to commercial processes. One important chemical conversion, which is difficult to achieve enantio- or enantiotopo- selectively, is the Baeyer-Villiger (BV) oxidation of ketones. Using cyclohexanone monooxygenase to catalyse the reaction produces optically pure esters and lactones with exquisite enantiomeric excess values. Recently, these enzymes and their many applications in synthetic chemistry have been explored. The scale-up of these conversions has been examined with the idea of implementing the first commercial Baeyer-Villiger monooxygenase-based process. Here, we review the state-of-the-art situation for the scale-up and exploitation of these enzymes.
引用
收藏
页码:318 / 323
页数:6
相关论文
共 51 条
[1]   ENZYMATIC BAEYER-VILLIGER TYPE OXIDATIONS OF KETONES CATALYZED BY CYCLOHEXANONE OXYGENASE [J].
ABRIL, O ;
RYERSON, CC ;
WALSH, C ;
WHITESIDES, GM .
BIOORGANIC CHEMISTRY, 1989, 17 (01) :41-52
[2]   MICROBIOLOGICAL TRANSFORMATIONS .22. MICROBIOLOGICALLY MEDIATED BAEYER-VILLIGER REACTIONS - A UNIQUE ROUTE TO SEVERAL BICYCLIC GAMMA-LACTONES IN HIGH ENANTIOMERIC PURITY [J].
ALPHAND, V ;
FURSTOSS, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1306-1309
[3]   Microbiological transformations .36. Preparative scale synthesis of chiral thioacetal and thioketal sulfoxides using whole-cell biotransformations [J].
Alphand, V ;
Gaggero, N ;
Colonna, S ;
Pasta, P ;
Furstoss, R .
TETRAHEDRON, 1997, 53 (28) :9695-9706
[4]   MICROBIAL TRANSFORMATIONS .16. ONE-STEP SYNTHESIS OF A PIVOTAL PROSTAGLANDIN CHIRAL SYNTHON VIA A HIGHLY ENANTIOSELECTIVE MICROBIOLOGICAL BAEYER-VILLIGER TYPE REACTION [J].
ALPHAND, V ;
ARCHELAS, A ;
FURSTOSS, R .
TETRAHEDRON LETTERS, 1989, 30 (28) :3663-3664
[5]   Microbiological transformations 44. Optimisation of a new Baeyer-Villigerase activity: application to the stereospecific oxidation of 3-phenylcyclobutanone [J].
Alphand, V ;
Furstoss, R .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2000, 9 (4-6) :209-217
[6]  
ALPHAND V, 2001, PRACTICAL APPROACH C, P214
[7]  
[Anonymous], ANGEW CHEM
[8]   Microbiological transformations. Part 51: The first example of a dynamic kinetic resolution process applied to a microbiological Baeyer-Villiger oxidation [J].
Berezina, N ;
Alphand, V ;
Furstoss, R .
TETRAHEDRON-ASYMMETRY, 2002, 13 (18) :1953-1955
[9]   Near-IR spectroscopic monitoring of analytes during microbially catalysed Baeyer-Villiger bioconversions [J].
Bird, PA ;
Sharp, DCA ;
Woodley, JM .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (04) :569-576
[10]  
Bolm C, 2001, SYNLETT, P1461