MODEL FOR THE FUNCTIONAL ACTIVE-SITE OF BAEYER-VILLIGERASES - X-RAY CRYSTAL DATA FOR 8-ENDO-BENZOYLOXY-N-(1'-PHENYLETHYL)BICYCLO[3.3.0] OCTANE-2-ENDO-CARBOXAMIDE

Authors
KELLY DR KNOWLES CJ MAHDI JG WRIGHT MA TAYLOR IN HIBBS DE HURSTHOUSE MB MISHAL AK ROBERTS SM WAN PWH GROGAN G WILLETTS AJ
Citation
Dr. Kelly et al., MODEL FOR THE FUNCTIONAL ACTIVE-SITE OF BAEYER-VILLIGERASES - X-RAY CRYSTAL DATA FOR 8-ENDO-BENZOYLOXY-N-(1'-PHENYLETHYL)BICYCLO[3.3.0] OCTANE-2-ENDO-CARBOXAMIDE, Journal of the Chemical Society. Perkin transactions. I, (16), 1995, pp. 2057-2066
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
16
Year of publication
1995
Pages
2057 - 2066
Database
ISI
SICI code
0300-922X(1995):16<2057:MFTFAO>2.0.ZU;2-Y
Abstract
An active-site model for enzyme-catalysed Baeyer-Villiger reactions is proposed and tested by transformation of the tricyclic ketone 6 to th e lactone 7 (> 98% ee) using purified enzymes from Acinetobacter sp. N CIMB 9871 and Pseudomonas putida NCIMB 10 007 (M01). The absolute ster eochemistry of the lactone 7 was determined by a single-crystal X-ray diffraction structure determination of the (1R')-alpha-methylbenzylami de benzoate derivative 11b. Baeyer-Villiger reactions (and Baeyer-Vill igerases) are classified by the stereochemistry of the active site and the hydroxy peroxide intermediates.