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Structure and stereochemistry of products of hydroxylation of human steroid hormones by a housefly cytochrome P450 (CYP6A1)

✍ Scribed by Neil E. Jacobsen; Katalin E. Kövér; Marat B. Murataliev; René Feyereisen; F. Ann Walker

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
171 KB
Volume
44
Category
Article
ISSN
0749-1581

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✦ Synopsis

The structure and stereochemistry of nine steroid metabolites isolated in quantities ranging from 0.15 to 1.8 mg were determined using a variety of NMR techniques, including heteronuclear multiple bond correlation (HMBC) using broadband adiabatic 13 C pulses and phase-sensitive data presentation. Testosterone, androstenedione and progesterone were oxidized with housefly cytochrome P450 6A1 enzyme reconstituted in vitro with housefly NADPH cytochrome P450 reductase and cytochrome b 5 . NMR analysis in CD 3 OD using a modified HMBC sequence as well as 2D heteronuclear single quantum correlation (HSQC), COSY and nuclear Overhauser and exchange spectroscopy (NOESY), combined with a detailed analysis of J couplings showed that hydroxylation occurs exclusively on the b-face of the steroids, at positions 2, 12, and 15.

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