BIOTRANSFORMATION OF ERGOT ALKALOIDS BY HALOPEROXIDASE FROM STREPTOMYCES-AUREOFACIENS - STEREOSELECTIVE ACETOXYLATION AND PROPIONOXYLATION

Authors
KREN V KAWULOKOVA L SEDMERA P POLASEK M LINDHORST TK VANPEE KH
Citation
V. Kren et al., BIOTRANSFORMATION OF ERGOT ALKALOIDS BY HALOPEROXIDASE FROM STREPTOMYCES-AUREOFACIENS - STEREOSELECTIVE ACETOXYLATION AND PROPIONOXYLATION, Liebigs Annalen, (11), 1997, pp. 2379-2383
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
11
Year of publication
1997
Pages
2379 - 2383
Database
ISI
SICI code
0947-3440(1997):11<2379:BOEABH>2.0.ZU;2-T
Abstract
Agroclavine (1) was oxidized, by haloperoxidase from Streptomyces aure ofaciens, to 2,3-dihyro-6,8-dimethyl-3 beta-acetoxy-8-ergolen-2-one (2 ) in the presence of sodium acetate and bromine ions. Acetate was inco rporated into the above product during oxidation. In a propionate buff er, incorporation of propionate into the product was observed, yieldin g 2,3-dihydro-6,8-dimethyl-3 beta-8-ergolen-2-one (4). The biotransfor mation proceeded faster in the propionate buffer, affording also the h igher oxidation product ,10b-hexahydro-2,4-dimethyl-6-oxobenzo[f]quino line (3).