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PMID: 6029605 Published · ppublish English Journal Article

The stereochemistry of the hydrogen elimination in the biological conversion of cholest-7-en-3-beta-ol into cholesterol.

The Biochemical journal ·Vol. 102 ·No. 2 ·1967-02-00 ·Pages 462-7

Akhtar M, Marsh S

Abstract

1. The syntheses of Delta(7)-[4-(14)C]cholestenol (XVI, Scheme 3) and Delta(7)-[6alpha-(3)H]-cholestenol (XII, Scheme 2) are described. 2. The metabolism of doubly labelled Delta(7)-cholestenol (II, Scheme 1) by rat-liver homogenates was studied. 3. During the enzymic conversion of Delta(7)-cholestenol into cholesterol (IV, Scheme 1) the 6alpha-hydrogen atom of the former is lost and the overall reaction corresponds to a cis-elimination. 4. In the light of these results various mechanisms for the conversion of Delta(7)-cholestenol into cholesterol are discussed.

MeSH Terms
Carbon Isotopes Chemical Phenomena Chemistry Chemistry, Organic Cholesterol/biosynthesis Hydrogen Organic Chemistry Phenomena Sterols Tritium
Chemicals
Carbon Isotopes Sterols Tritium Hydrogen Cholesterol
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Akhtar M
Marsh S
References (5)
5 references, click to expand
  1. Pathways of enzymic synthesis and conversion to cholesterol of delta-5,7,24-cholestatrien-3 beta-ol and other naturally occurring sterols.
    J Biol Chem. 1965 Nov;240(11):4176-88 PMID: 4378934
  2. A convenient synthesis of (9,19-3H2)cholecalciferol 3,5-dinitrobenzoate and the mechanism of the precholecalciferol to calciferol reaction.
    J Chem Soc Perkin 1. 1965 Sep;:5964-8 PMID: 4284866
  3. Metabolic transformation of cholestenediols.
    J Biol Chem. 1965 Dec;240(12):4598-602 PMID: 5846981
  4. Agents affecting lipid metabolism. 28. A 7-dehydrocholesterol delta-7-reductase inhibitor (AY-9944) as tool in studies of delta-7-sterol metabolism.
    Biochemistry. 1966 Mar;5(3):1060-4 PMID: 5911284
  5. Conversion of delta7-cholestenol-4-C-14 and 7-dehydro-cholesterol-4-C-14 to cholesterol.
    J Biol Chem. 1961 Dec;236:3137-40 PMID: 13909337
Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
0264-6021
Published
1967-02-00
Pages
462-7
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC1270267
Subset
IM
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