Preparation of both enantiomers of a chiral lactone through combined microbiological reduction and oxidation
作者： Jamal Ouazzani-Chahdi , Didier Buisson , Robert Azerad
DOI: 10.1016/S0040-4039(00)95923-9
关键词:
摘要: The Baeyer-Villiger-like oxidation of (R,S)-2,2,5,5-tetramethyl-4-hydroxy -cyclohexanone by several fungal strains was highly enantioselective, affording a rearranged (S)-hydroxy-γ-lactone. recovery the nearly optically pure (R)-hydroxyketone allowed its conversion to enantiomeric (R)-hydroxylactone through classical Baeyer-Villiger oxidation.
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sci-hub.se 参考文章(20)
H.E. Conrad, René DuBus, M.J. Namtvedt, I.C. Gunsalus, Mixed Function Oxidation II. SEPARATION AND PROPERTIES OF THE ENZYMES CATALYZING CAMPHOR LACTONIZATION Journal of Biological Chemistry. ,vol. 240, pp. 495- 503 ,(1965) , 10.1016/S0021-9258(18)97679-9
Michael K. Trower, R. Martin Buckland, Raymond Higgins, Martin Griffin, Isolation and Characterization of a Cyclohexane-Metabolizing Xanthobacter sp Applied and Environmental Microbiology. ,vol. 49, pp. 1282- 1289 ,(1985) , 10.1128/AEM.49.5.1282-1289.1985
C.A. Yu, I.C. Gunsalus, Monoxygenases. VII. Camphor ketolactonase I and the role of three protein components. Journal of Biological Chemistry. ,vol. 244, pp. 6149- 6152 ,(1969) , 10.1016/S0021-9258(18)63518-5
D G Taylor, P W Trudgill, Camphor revisited: studies of 2,5-diketocamphane 1,2-monooxygenase from Pseudomonas putida ATCC 17453. Journal of Bacteriology. ,vol. 165, pp. 489- 497 ,(1986) , 10.1128/JB.165.2.489-497.1986
Martin Griffin, Peter W. Trudgill, The metabolism of cyclopentanol by Pseudomonas N.C.I.B. 9872. Biochemical Journal. ,vol. 129, pp. 595- 603 ,(1972) , 10.1042/BJ1290595
D. B. Norris, P. W. Trudgill, The metabolism of cyclohexanol by Nocardia globerula CL1. Biochemical Journal. ,vol. 121, pp. 363- 370 ,(1971) , 10.1042/BJ1210363
Eiji ITAGAKI, Studies on steroid monooxygenase from Cylindrocarpon radicicola ATCC 11011. Oxygenative lactonization of androstenedione to testololactone. Journal of Biochemistry. ,vol. 99, pp. 825- 832 ,(1986) , 10.1093/OXFORDJOURNALS.JBCHEM.A135542
Eiji ITAGAKI, Studies on steroid monooxygenase from Cylindrocarpon radicicola ATCC 11011. Purification and characterization. Journal of Biochemistry. ,vol. 99, pp. 815- 824 ,(1986) , 10.1093/OXFORDJOURNALS.JBCHEM.A135541
Nuala A. DONOGHUE, David B. NORRIS, Peter W. TRUDGILL, The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871. FEBS Journal. ,vol. 63, pp. 175- 192 ,(1976) , 10.1111/J.1432-1033.1976.TB10220.X
H.E. Conrad, Rene DuBus, I.C. Gunsalus, An enzyme system for cyclic ketone lactonization Biochemical and Biophysical Research Communications. ,vol. 6, pp. 293- 297 ,(1961) , 10.1016/0006-291X(61)90382-5