A study of the membrane bound enzymes involved in oestrogen biosynthesis
A study of the membrane bound enzymes involved in oestrogen biosynthesis
The biosynthesis of 3-hydroxy-1,3,5(1O)-oestratriene17-one in human full term placenta may be regarded as commencing from the C-19 steroid, 36-hydroxy-5-androstene17-one. The elaboration of the aromatic "A" ring in 3-hydroxy-1,3,5, (10)-oestratriene-l7-one from the A5-30-hydroxy system, is achieved in two stage an anaerobic and an aerobic stage. In the anaerobic stage the A5-30-hydroxy system of 38-hydroxy-5-androstene-17-one is converted into the a4-3-oxo functionality of 4-androstene-3,17-dione. This process has been shown to proceed via the elimination of the 46-hydrogen followed by reprotonation of the proposed A3'5-dienol in the 63 position. The C-19 demethylation of the a4-3-oxo steroid, 4-androstene-3,17-dione to produce 3-hydroxy-1,3,5, (10)-oestratriene-17-one constitutes the aerobic stage and involves the participation of three oxygen dependant reactions. Several facets of these reactions have been studied. In the final section of this thesis attempts have been made to gain information about the multiplicity of hydroxylation catalytic sites in the placental aromatase complex by synthesizing and testing a number of C-10 andC-19 functionalized analogues of 19-hydroxy and 19-oxo-4-androstene-3,17-dione. Finally the mechanism of action of the aromatase complexes obtained from placental endoplasmic reticulum and placental mitochondria have been compared.
University of Southampton
1982
Calder, Michael Roger
(1982)
A study of the membrane bound enzymes involved in oestrogen biosynthesis.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The biosynthesis of 3-hydroxy-1,3,5(1O)-oestratriene17-one in human full term placenta may be regarded as commencing from the C-19 steroid, 36-hydroxy-5-androstene17-one. The elaboration of the aromatic "A" ring in 3-hydroxy-1,3,5, (10)-oestratriene-l7-one from the A5-30-hydroxy system, is achieved in two stage an anaerobic and an aerobic stage. In the anaerobic stage the A5-30-hydroxy system of 38-hydroxy-5-androstene-17-one is converted into the a4-3-oxo functionality of 4-androstene-3,17-dione. This process has been shown to proceed via the elimination of the 46-hydrogen followed by reprotonation of the proposed A3'5-dienol in the 63 position. The C-19 demethylation of the a4-3-oxo steroid, 4-androstene-3,17-dione to produce 3-hydroxy-1,3,5, (10)-oestratriene-17-one constitutes the aerobic stage and involves the participation of three oxygen dependant reactions. Several facets of these reactions have been studied. In the final section of this thesis attempts have been made to gain information about the multiplicity of hydroxylation catalytic sites in the placental aromatase complex by synthesizing and testing a number of C-10 andC-19 functionalized analogues of 19-hydroxy and 19-oxo-4-androstene-3,17-dione. Finally the mechanism of action of the aromatase complexes obtained from placental endoplasmic reticulum and placental mitochondria have been compared.
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Published date: 1982
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Local EPrints ID: 460046
URI: http://eprints.soton.ac.uk/id/eprint/460046
PURE UUID: 4ffc2b68-dd45-4fc1-b762-40d37470360a
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Date deposited: 04 Jul 2022 17:44
Last modified: 04 Jul 2022 17:44
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Author:
Michael Roger Calder
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