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Introduction of a 16α-hydroxyl function into estrone by Streptomyces roseochromogenes

✍ Scribed by Dr. M. Iida; H. Iizuka

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 271 KB
Volume: 17
Category: Article
ISSN: 0233-111X
DOI: 10.1002/jobm.19770170703

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✦ Synopsis

Abstract

Streptomyces roseochromogenes (NRRL B‐1233) converted estrone predominantly into its 16α‐hydroxyl derivative. Chemical and spectroscopic (UV, IR, NMR, MS) methods were used in establishing the structure and stereochemistry of the oxidation product. The product was assigned as 16α‐hydroxyestrone (yield, 17%). No other oxidation product was detected in this experiment. An interrelationship between cell growth and 16α‐hydroxy‐estrone formation was observed. Also, 16α‐hydroxylation of estrone was observed in resting cells

16α‐Hydroxylase showed good activity at 3.7 × 10^−4^M of estrone concentration and was completely inhibited by 1.1 × 10^−3^M. These results indicate the presence of a constitutive 16α‐hydroxylase in the organism investigated.

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Microbial introduction of a 16whydroxyl function into the steroid nucleus (EiuLqeqcrtcqrii u t i i 18. 12. JYih') Tlie iritiodrrction of a 1Ka-liydroxyl function into t h r strroid nucleiis n as studied in resting ~~~1 1 s o f Ntrrpfonryces roseochrotnogenes N RKI, l3-1233. The oxidation product of