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Synthesis of [2‐d]estradiol, [4‐d]estradiol, [2‐t]estradiol and [4‐t]estradiol with high specificity
Author(s) -
Porubek David J.,
Namkung Moses J.,
Juchau Mont R.,
Nelson Sidney D.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210803
Subject(s) - chemistry , tritium , deuterium , halogenation , ethanol , tritium illumination , steroid , specific activity , radiochemistry , stereochemistry , chromatography , hormone , organic chemistry , biochemistry , enzyme , physics , quantum mechanics , nuclear physics
17‐β‐Estradiol has been labeled in the 2 or 4 position with tritium or deuterium. Both 2‐ and 4‐iodoestradiol were prepared by treatment of estradiol with N‐iodosuccinimide in ethanol followed by chromatographic separation. Reductive dehalogenation of 2‐ and 4‐iodoestradiol with tritium gas gave [2‐t] estradiol and [4‐t] estradiol, respectively, with specific activities of approximately 2 Ci/mmole. Greater than 99% of the radiolabel was incorporated into the target positions as determined by rehalogenation of the radiolabeled compounds. Analysis of the deuterium labeled compounds, [2‐d] estradiol and [4‐d] estradiol, similarly prepared by reduction with deuterium gas, revealed that isotope incorporation was high and specific.