Baeyer-Villiger oxidations catalyzed by engineered microorganisms: Enantioselective synthesis of δ-valerolactones with functionalized chains

被引：0

作者：

Wang, Shaozhao ^{[1
]}

Chen, Gang ^{[1
]}

Kayser, Margaret M. ^{[1
]}

Iwaki, Hiroaki ^{[1
]}

Lau, Peter C.K. ^{[1
]}

Hasegawa, Yoshie ^{[1
]}

机构：

[1] Department of Physical Sciences, University of New Brunswick, Saint John, NB E2L 4L5, Canada

来源：

| 2002年 / National Research Council of Canada卷 / 80期

关键词：

Escherichia coli - Microorganisms - Oxidation - Yeast;

D O I：

10.1139/v02-035

中图分类号：

学科分类号：

摘要：

Cyclohexanone monooxygenase (CHMO) from Acinetobacter sp NCIMB 9871 expressed in baker's yeast and in E. coli and cyclopentanone monooxygenase (CPMO) from Comamonas (previously Pseudomonas) sp. NCIMB 9872 expressed in E. coli are new bioreagents for Baeyer-Villiger oxidations. These engineered microorganisms, requiring neither biochemical expertise nor equipment beyond that found in chemical laboratories, were evaluated as reagents for Baeyer-Villiger oxidations of cyclopentanones substituted at the 2-position with polar and nonpolar chains suitable for further modifications. Two such functionalized substrates that can be transformed into highly enantiopure lactones were identified. The performance and the potential of these bioreagents are discussed.

引用

共 50 条

[41] Bioreduction of (R)-carvone and regioselective Baeyer-Villiger oxidations:: Application to the asymmetric synthesis of cryptophycin fragment A
Varie, DL
Brennan, J
Briggs, B
Cronin, JS
Hay, DA
Rieck, JA
Zmijewski, MJ
TETRAHEDRON LETTERS, 1998, 39 (46) : 8405 - 8408
[42] Applications of Baeyer-Villiger Monooxygenases in Organic Synthesis
Alphand, Veronique
Wohlgemuth, Roland
CURRENT ORGANIC CHEMISTRY, 2010, 14 (17) : 1928 - 1965
[43] Baeyer-Villiger monooxygenases in aroma compound synthesis
Fink, Michael J.
Rudroff, Florian
Mihovilovic, Marko D.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (20) : 6135 - 6138
[44] Applications of Baeyer-Villiger monooxygenase in organic synthesis
Jiang, B
Luo, J
Huang, H
Chen, Y
Li, ZY
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (10) : 1198 - 1207
[45] SYNTHESIS OF (±)-CEPHALANTHRIN A USING BAEYER-VILLIGER OXIDATION
Itoh, Tomoki
Abe, Takumi
Choshi, Tominari
Nishiyama, Takashi
Ishikura, Minoru
HETEROCYCLES, 2017, 95 (01) : 507 - 516
[46] Green production of indigo and indirubin by an engineered Baeyer-Villiger monooxygenase
Catucci, Gianluca
Turella, Simone
Cheropkina, Hanna
De Angelis, Melissa
Gilardi, Gianfranco
Sadeghi, Sheila J.
BIOCATALYSIS AND AGRICULTURAL BIOTECHNOLOGY, 2022, 44
[47] BIOTRANSFORMATIONS BY FUNGI - REGIOSELECTIVE PLUS STEREOSELECTIVE BAEYER-VILLIGER OXIDATIONS BY DEMATIACEOUS FUNGI
CARNELL, A
WILLETTS, A
BIOTECHNOLOGY LETTERS, 1992, 14 (01) : 17 - 20
[48] PLATINUM-CATALYZED OXIDATIONS WITH HYDROGEN-PEROXIDE - ENANTIOSPECIFIC BAEYER-VILLIGER OXIDATION OF CYCLIC-KETONES
GUSSO, A
BACCIN, C
PINNA, F
STRUKUL, G
ORGANOMETALLICS, 1994, 13 (09) : 3442 - 3451
[49] Divorce in the two-component BVMO family: the single oxygenase for enantioselective chemo-enzymatic Baeyer-Villiger oxidations
Rollig, Robert
Paul, Caroline E.
Claeys-Bruno, Magalie
Duquesne, Katia
Kara, Selin
Alphand, Veronique
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (15) : 3441 - 3450
[50] Use of theoretical chemistry to explain Baeyer-Villiger oxidations of methoxy aromatic aldehydes
Anoune, N
Hannachi, H
Lanteri, P
Longeray, R
Arnaud, C
JOURNAL OF CHEMICAL EDUCATION, 1998, 75 (10) : 1290 - 1293

← 1 2 3 4 5 →