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Literature DB >> 6029605

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

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.

Entities: Chemical Gene Species

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Year: 1967 PMID： 6029605 PMCID： PMC1270267 DOI： 10.1042/bj1020462

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

5 in total

1. Pathways of enzymic synthesis and conversion to cholesterol of delta-5,7,24-cholestatrien-3 beta-ol and other naturally occurring sterols.

Authors: M E Dempsey
Journal: J Biol Chem Date: 1965-11 Impact factor: 5.157

2. A convenient synthesis of (9,19-3H2)cholecalciferol 3,5-dinitrobenzoate and the mechanism of the precholecalciferol to calciferol reaction.

Authors: M Akhtar; C J Gibbons
Journal: J Chem Soc Perkin 1 Date: 1965-09

3. Metabolic transformation of cholestenediols.

Authors: M Slaytor; K Bloch
Journal: J Biol Chem Date: 1965-12 Impact factor: 5.157

4. Agents affecting lipid metabolism. 28. A 7-dehydrocholesterol delta-7-reductase inhibitor (AY-9944) as tool in studies of delta-7-sterol metabolism.

Authors: D Dvornik; M Kraml; J F Bagli
Journal: Biochemistry Date: 1966-03 Impact factor: 3.162

5. Conversion of delta7-cholestenol-4-C-14 and 7-dehydro-cholesterol-4-C-14 to cholesterol.

Authors: G J SCHROEPFER; I D FRANTZ
Journal: J Biol Chem Date: 1961-12 Impact factor: 5.157

5 in total

11 in total

6. The conversion of cholest-7-en-3beta-ol into cholesterol. General comments on the mechanism of the introduction of double bonds in enzymic reactions.

Authors: S M Dewhurst; M Akhtar
Journal: Biochem J Date: 1967-12 Impact factor: 3.857

7. The incorporation of a hydrogen atom at C-15 of cholesterol biosynthesized from squalene.

Authors: M Akhtar; A D Rahimtula; D C Wilton
Journal: Biochem J Date: 1969-10 Impact factor: 3.857

8. Incorporation of (2-14C, (5r)-5-3H1) mevalonic acid into cholesterol by a rat liver homogenate and into beta-sitosterol and 28-isofucosterol by larix decidua leaves.

Authors: L J Goad; G F Gibbons; L M Bolger; H H Rees; T W Goodwin
Journal: Biochem J Date: 1969-10 Impact factor: 3.857

9. The mechanism of the elaboration of ring B in ergosterol biosynthesis.

Authors: M Akhtar; M A Parvez
Journal: Biochem J Date: 1968-07 Impact factor: 3.857

10. 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

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

1. Pathways of enzymic synthesis and conversion to cholesterol of delta-5,7,24-cholestatrien-3 beta-ol and other naturally occurring sterols.

2. A convenient synthesis of (9,19-3H2)cholecalciferol 3,5-dinitrobenzoate and the mechanism of the precholecalciferol to calciferol reaction.

3. Metabolic transformation of cholestenediols.

4. Agents affecting lipid metabolism. 28. A 7-dehydrocholesterol delta-7-reductase inhibitor (AY-9944) as tool in studies of delta-7-sterol metabolism.

5. Conversion of delta7-cholestenol-4-C-14 and 7-dehydro-cholesterol-4-C-14 to cholesterol.

Review 1. Biosynthesis of carotenoids and plant triterpenes.

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

3. The stereochemistry of hydrogen elimination during 7,8-double bond formation by Tetrahymena pyriformis.

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

5. The role of a 5alpha-hydroxylated intermediate in the formation of the 5, 6-double bond in cholesterol biosynthesis.

6. The conversion of cholest-7-en-3beta-ol into cholesterol. General comments on the mechanism of the introduction of double bonds in enzymic reactions.

7. The incorporation of a hydrogen atom at C-15 of cholesterol biosynthesized from squalene.

8. Incorporation of (2-14C, (5r)-5-3H1) mevalonic acid into cholesterol by a rat liver homogenate and into beta-sitosterol and 28-isofucosterol by larix decidua leaves.

9. The mechanism of the elaboration of ring B in ergosterol biosynthesis.

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