ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Microbial Transformations of Steroids, XV: Microbial Hydroxylation of 3α-Acetoxy-5β-pregnane-20-carboxylic Acid and of its Methyl Ester by Calonectria decora and Syncephalastrum racemosum3α-Acetoxy-5β-pregnane-20-carboxylic Acid (1) is hydroxylated by fermentation with Calonectria decora in 12β- (3), 7β,11β- (4), and 1β,12β-position (5) with hydrolysis of the 3-acetoxy group. The methyl ester 2 is attacked in 7α,12β- (6), 7β, 11α- (7), and 12β,15α-position (8), Syncephalastrum racemosum forms from 1 the hydroxy products in positions 11β (9), 12β (3), 7β,11β (4), and 11β,15β (10) as well as the further transformation products 3α-hydroxy- (13), 3α,11β-dihydroxy- (14), 3α,12β-dihydroxy-5β,20α-pregnane-20,18-carbolactone (11), and 11,18-epoxy-3α-hydroxy-5β,20α-pregnane-20,18-carbolactone (16), 1 is transformed by Mycobacterium smegmatis into methyl 3-oxo-pregnane- (18) and 3-oxo-1,4-pregnadiene-20-carboxylate (20).
Notes:
3α-Acetoxy-5β-pregnan-20-carbonsäure (1) wird durch Fermentation mit Calonectria decora unter Verseifung der 3-Acetylgruppe in 12β- (3), 7β,11β- (4) und 1β,12β-Stellung (5) hydroxyliert. Der Methylester 2 wird analog in 7α,12β- (6), 7β,11α- (7) und 12β, 15α-Position (8) angegriffen. Syncephalastrum racemosum bildet aus 1 die Hydroxylierungsprodukte in den Positionen 11β (9), 12β (3), 7β,11β (4) und 11β,15β (10) sowie die weiteren Umwandlungsprodukte 3α-Hydroxy- (13), 3α,11β-Dihydroxy- (14), 3α,12β-Dihydroxy-5β,20α-pregnan-20,18-carbolacton (11) sowie 11,18-Expoxy-3α-hydroxy-5β,20α-pregnan-20,18-carbolacton (16). Durch Mycobacterium smegmatis wird 1 zu 3-Oxo-4-pregnen- (18) und 3-Oxo-1,4-pregnadien-20-carbonsäure-methylester (20) umgewandelt.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19781110611
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