Chemo-enzymatic Baeyer-Villiger oxidation of cyclopentanone and substituted cyclopentanones

被引:35
作者
Rios, Maria Yolanda [1 ]
Salazar, Enrique [1 ]
Olivo, Horacio F. [1 ]
机构
[1] Univ Iowa, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA
基金
美国国家科学基金会;
关键词
chemo-enzymatic oxidation; Candida antarctica lipase-B; Baeyer-Villiger oxidation; trans-esterification;
D O I
10.1016/j.molcatb.2007.12.012
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Chemo-enzymatic oxidation of cyclopentanones and substituted cyclopentanones to the corresponding delta-valerolactones was investigated employing catalytic a mount of Candida antarctica lipase-B in ethyl acetate and employing urea-hydrogen peroxide its the oxidant. In contrast to the smooth oxidation of cyclohexanones to the corresponding epsilon-caprolactones, the delta-valerolactones reacted further with the lipase delivering trans-esterified products and also acetylated alcohols, depending on the structural nature of the cyclopentanones, (C) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:61 / 66
页数:6
相关论文
共 46 条
[1]   One biocatalyst - Many applications: The use of Candida antarctica B-lipase in organic synthesis [J].
Anderson, EM ;
Karin, M ;
Kirk, O .
BIOCATALYSIS AND BIOTRANSFORMATION, 1998, 16 (03) :181-204
[2]   Lipase-mediated epoxidation utilizing urea-hydrogen peroxide in ethyl acetate [J].
Ankudey, Emanuel G. ;
Olivo, Horacio F. ;
Peeples, Tonya L. .
GREEN CHEMISTRY, 2006, 8 (10) :923-926
[3]   LIPASE CATALYZED SYNTHESIS OF PEROXYCARBOXYLIC ACIDS AND LIPASE MEDIATED OXIDATIONS [J].
BJORKLING, F ;
FRYKMAN, H ;
GODTFREDSEN, SE ;
KIRK, O .
TETRAHEDRON, 1992, 48 (22) :4587-4592
[4]   LIPASE-MEDIATED FORMATION OF PEROXYCARBOXYLIC ACIDS USED IN CATALYTIC EPOXIDATION OF ALKENES [J].
BJORKLING, F ;
GODTFREDSEN, SE ;
KIRK, O .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (19) :1301-1303
[5]   OPTICALLY-ACTIVE LACTONES FROM A BAEYER-VILLIGER-TYPE METAL-CATALYZED OXIDATION WITH MOLECULAR-OXYGEN [J].
BOLM, C ;
SCHLINGLOFF, G ;
WEICKHARDT, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18) :1848-1849
[6]  
Bornscheuer UT, 2006, HYDROLASES IN ORGANIC SYNTHESIS: REGIO- AND STEREOSELECTIVE BIOTRANSFORMATIONS, 2ND EDITION, P1
[7]   Hydrolase-catalysed synthesis of peroxycarboxylic acids:: Biocatalytic promiscuity for practical applications [J].
Carboni-Oerlemans, Chiara ;
Dominguez de Maria, Pablo ;
Tuin, Bernard ;
Bargeman, Gerrald ;
van der Meer, Ab ;
van Gemert, Robert .
JOURNAL OF BIOTECHNOLOGY, 2006, 126 (02) :140-151
[8]   Key green chemistry research areas - a perspective from pharmaceutical manufacturers [J].
Constable, David J. C. ;
Dunn, Peter J. ;
Hayler, John D. ;
Humphrey, Guy R. ;
Leazer, Johnnie L., Jr. ;
Linderman, Russell J. ;
Lorenz, Kurt ;
Manley, Julie ;
Pearlman, Bruce A. ;
Wells, Andrew ;
Zaks, Aleksey ;
Zhang, Tony Y. .
GREEN CHEMISTRY, 2007, 9 (05) :411-420
[9]   OXIDATION REACTIONS USING UREA HYDROGEN-PEROXIDE - A SAFE ALTERNATIVE TO ANHYDROUS HYDROGEN-PEROXIDE [J].
COOPER, MS ;
HEANEY, H ;
NEWBOLD, AJ ;
SANDERSON, WR .
SYNLETT, 1990, (09) :533-535
[10]   Biocatalytic properties of Baeyer-Villiger monooxygenases in aqueous-organic media [J].
de Gonzalo, G ;
Ottolina, G ;
Zambianchi, F ;
Fraaije, MW ;
Carrea, G .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2006, 39 (1-4) :91-97