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Pregnenolone‐17 α− 3 H. Synthesis and study of label distribution
Author(s) -
Milewich Leon,
Axelrod Leonard R.
Publication year - 1971
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590070202
Subject(s) - pregnenolone , chemistry , acetic acid , zinc , deuterium , radiochemistry , medicinal chemistry , metal , nuclear chemistry , inorganic chemistry , organic chemistry , steroid , biochemistry , physics , quantum mechanics , hormone
Pregnenolone‐17α − 3 H was synthesized by reaction of 17α‐bromo‐pregnenolone with tritiated acetic acid (CH 3 CO 2 3 H) and zinc metal dust. The distribution of the label in the product was studied; about 98% was at the 17‐position and the remainder was randomly distributed on the steroids nucleus. It was also found that when pregnenolone was stirred with deuterated acetic acid (CH 3 CO 2 2 H) and zinc metal dust for a longer period of time (22 hr) and in relatively high concentration, the protons of the C 21 ‐methyl group (˜57%) were exchanged for deuterium.