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Literature DB >> 5419748

The stereochemistry of hydrogen elimination from C-7 in cholesterol and ergosterol biosynthesis.

Abstract

The synthesis of [7alpha-(3)H]lanosterol is described. It is shown that in the conversion of [7alpha-(3)H,26,27-(14)C(2)]lanosterol into cholesterol by a rat liver system, it is the 7beta-hydrogen atom that is predominantly removed. On the other hand, the conversion of doubly labelled lanosterol into ergosterol by whole yeast cells results in the loss of the 7alpha-hydrogen atom. These results therefore suggest that the C-7 hydrogen atoms with opposite stereochemistry are labilized by the rat liver and the yeast Delta(8)-Delta(7) steroid isomerases.

Entities: Chemical Gene Species

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Year: 1970 PMID： 5419748 PMCID： PMC1178958 DOI： 10.1042/bj1170539

Source DB: PubMed Journal: Biochem J ISSN： 0264-6021 Impact factor: 3.857

13 in total

1. The biological conversion of 7-dehydrocholesterol into cholesterol and comments on the reduction of double bonds.

Authors: D C Wilton; K A Munday; S J Skinner; M Akhtar
Journal: Biochem J Date: 1968-02 Impact factor: 3.857

2. Studies in phytosterol biosynthesis. Mechanism of biosynthesis of cycloartenol.

Authors: H H Rees; L J Goad; T W Goodwin
Journal: Biochem J Date: 1968-04 Impact factor: 3.857

3. Studies on the biosynthesis of cholesterol. XX. Steric course of decarboxylation of 5-pyrophosphomevalonate and of the carbon to carbon bond formation in the biosynthesis of farnesyl pyrophosphate.

Authors: J W Cornforth; R H Cornforth; G Popják; L Yengoyan
Journal: J Biol Chem Date: 1966-09-10 Impact factor: 5.157

4. The biological conversion of 5alpha-cholest-8-en-3beta-ol to 5alpha-cholest-7-en-3beta-ol in the biosynthesis of cholesterol.

Authors: L Canonica; A Fiecchi; M G Kienle; A Scala; G Galli; E G Paoletti; R Paoletti
Journal: Steroids Date: 1968-03 Impact factor: 2.668

5. Stereochemistry of tritium at C-1 and C-7 in cholesterol derived from (3R,2R)-2T-mevalonic acid.

Authors: E Caspi; J B Greig; P J Ramm; K R Varma
Journal: Tetrahedron Lett Date: 1968-07 Impact factor: 2.415

6. The role of a cholesta-8,14-dien-3-beta-ol system in cholesterol biosynthesis.

Authors: M Akhtar; I A Watkinson; A D Rahimtula; D C Wilton; K A Munday
Journal: Biochem J Date: 1969-03 Impact factor: 3.857

7. Studies on the biosynthesis of ergosterol in yeast. Formation of methylated intermediates.

Authors: H Katsuki; K Bloch
Journal: J Biol Chem Date: 1967-01-25 Impact factor: 5.157

8. The transfer of hydrogen from C-24 to C-25 in ergosterol biosynthesis.

Authors: M Akhtar; P F Hunt; M A Parvez
Journal: Biochem J Date: 1967-06 Impact factor: 3.857

9. The introduction of the C-22-C-23 ethylenic linkage in ergosterol biosynthesis.

Authors: M Akhtar; M A Parvez; P F Hunt
Journal: Biochem J Date: 1968-02 Impact factor: 3.857

10. Studies on the mechanism of the enzymatic conversion of delta 8-cholesten-3 beta-ol to delta 7-cholesten-3 beta-ol.

Authors: W H Lee; R Kammereck; B N Lutsky; J A McCloskey; G J Schroepfer
Journal: J Biol Chem Date: 1969-04-25 Impact factor: 5.157

5 in total

1. Sterol metabolism.

Authors: Pierre Benveniste
Journal: Arabidopsis Book Date: 2002-03-27

2. Different approaches toward an automatic structural alignment of drug molecules: applications to sterol mimics, thrombin and thermolysin inhibitors.

Authors: G Klebe; T Mietzner; F Weber
Journal: J Comput Aided Mol Des Date: 1994-12 Impact factor: 3.686