Synthesis of 16 alpha-/sub 3/H androgen and estrogen substrates for 16 alpha-hydroxylase
Journal Article
·
· Steroids; (United States)
The synthesis of 16 alpha-/sup 3/H androgens and estrogens is described. 1-(/sup 3/H)-Acetic acid in the presence of zinc dust reacts with 16 alpha-bromo-17-ketosteroids to produce 16 alpha-/sup 3/H-17-ketosteroids. This chemical reaction was used to prepare 16 alpha-/sup 3/H-dehydroepiandrosterone (I) and 16 alpha-/sub 4/H-estrone acetate (XI) from 16 alpha-bromo-dehydroepiandrosterone (X) and from 16 alpha-bromo-estrone acetate (XII), respectively. Using appropriate microbiological techniques, it was possible to convert these radiolabelled substrates into 16 alpha-/sup 3/H-androstenedione (II) and 16 alpha-/sup 3/H-estradiol-17 beta (VII). 16 alpha-/sup 3/H-Estrone (VI) was obtained by the chemical hydrolysis of 16 alpha-/sup 3/H-estrone acetate. The label distribution as determined by microbiological 16 alpha-hydroxylations indicated a specific labelling of 77% for androgens and 65% for estrogens in the 16 alpha position. These substrates can be used for measuring the 16 alpha hydroxylase activity, an important step in the biosynthesis of estriol (VIII) and estetrol (IX).
- OSTI ID:
- 5504465
- Journal Information:
- Steroids; (United States), Journal Name: Steroids; (United States) Vol. 37:2; ISSN STEDA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ANDROGENS
ANDROSTANES
CHEMICAL PREPARATION
ENZYME ACTIVITY
ENZYMES
ESTROGENS
FUNGI
HORMONES
HYDROXYLASES
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
MEASURING METHODS
MICROORGANISMS
ORGANIC COMPOUNDS
OXIDOREDUCTASES
PLANTS
SACCHAROMYCES
STEROID HORMONES
STEROIDS
SYNTHESIS
TRACER TECHNIQUES
TRITIUM COMPOUNDS
YEASTS
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
ANDROGENS
ANDROSTANES
CHEMICAL PREPARATION
ENZYME ACTIVITY
ENZYMES
ESTROGENS
FUNGI
HORMONES
HYDROXYLASES
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
MEASURING METHODS
MICROORGANISMS
ORGANIC COMPOUNDS
OXIDOREDUCTASES
PLANTS
SACCHAROMYCES
STEROID HORMONES
STEROIDS
SYNTHESIS
TRACER TECHNIQUES
TRITIUM COMPOUNDS
YEASTS