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Literature DB >> 5783476

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

M Akhtar, I A Watkinson, A D Rahimtula, D C Wilton, K A Munday.

Abstract

The biosynthesis of cholesterol from squalene and tritiated water is described. Degradation of the cholesterol indicated that C-15 may be involved in cholesterol biosynthesis. In accordance with this view it is shown that in the conversion of [2RS-(3)H(2)]mevalonic acid into cholesterol one of the hydrogen atoms at C-15 is removed. A mechanism for the removal of the 14alpha-methyl group in steroid biosynthesis that involves the labilization of a C-15 hydrogen atom is outlined. In accordance with the requirement of this scheme it is shown that 4,4'-dimethyl-cholesta-8,14-dien-3beta-ol is converted into cholesterol.

Entities: Chemical Gene

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Year: 1969 PMID： 5783476 PMCID： PMC1187605 DOI： 10.1042/bj1110757

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

8 in total

1. Synthesis of isomeric 4,4-dimethylcholestenols and identification of a lanosterol metabolite.

Authors: F GAUTSCHI; K BLOCH
Journal: J Biol Chem Date: 1958-12 Impact factor: 5.157

2. On the demethylation of lanosterol to cholesterol.

Authors: J A OLSON; M LINDBERG; K BLOCH
Journal: J Biol Chem Date: 1957-06 Impact factor: 5.157

3. 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

4. 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

5. The fate of the 15-beta hydrogen of lanosterol in cholesterol biosynthesis.

Authors: L Canonica; A Fiecchi; M G Kienle; A Scala; G Galli; E G Paoletti; R Paoletti
Journal: J Am Chem Soc Date: 1968-06-19 Impact factor: 15.419

6. The synthesis of tritium-labeled 14-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol and its enzymatic demethylation.

Authors: J C Knight; P D Klein; P A Szczepanik
Journal: J Biol Chem Date: 1966-04-10 Impact factor: 5.157

7. 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

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

Authors: M Akhtar; S Marsh
Journal: Biochem J Date: 1967-02 Impact factor: 3.857

8 in total

1. Chemical and enzymic studies on the characterization of intermediates during the removal of the 14alpha-methyl group in cholesterol biosynthesis. The use of 32-functionalized lanostane derivatives.

Authors: M Akhtar; K Alexander; R B Boar; J F McGhie; D H Barton
Journal: Biochem J Date: 1978-03-01 Impact factor: 3.857

5. Metabolism of 2,4 -3H - 14alpha-methyl -5alpha-ergost - 8-enol and 2,4- 3H- 5 alpha- ergosta-8, 14-dienol in chlorella ellipsoidea.

Authors: L B Tsai; G W Patterson; C F Cohen
Journal: Lipids Date: 1974-12 Impact factor: 1.880

6. Metabolism of 2,4-3H-14alpha-methyl-5alpha-ergost-8-enol and 2,4-3H-5alpha-ergosta-8,14-dienol in Ochromonas malhamensis.

Authors: J H Adler; G W Patterson
Journal: Lipids Date: 1976-08 Impact factor: 1.880

7. The intermediary role of a steroid 8,14-dien-3-beta-ol system in ergosterol biosynthesis.

Authors: M Akhtar; W A Brooks; I A Watkinson
Journal: Biochem J Date: 1969-11 Impact factor: 3.857

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

Authors: M Akhtar; A D Rahimtula; D C Wilton
Journal: Biochem J Date: 1970-04 Impact factor: 3.857

8 in total

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

1. Synthesis of isomeric 4,4-dimethylcholestenols and identification of a lanosterol metabolite.

2. On the demethylation of lanosterol to cholesterol.

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

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

5. The fate of the 15-beta hydrogen of lanosterol in cholesterol biosynthesis.

6. The synthesis of tritium-labeled 14-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol and its enzymatic demethylation.

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

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

1. Chemical and enzymic studies on the characterization of intermediates during the removal of the 14alpha-methyl group in cholesterol biosynthesis. The use of 32-functionalized lanostane derivatives.

Review 2. Biosynthesis of carotenoids and plant triterpenes.

3. The formation and reduction of the 14,15-double bond in cholesterol biosynthesis.

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

5. Metabolism of 2,4 -3H - 14alpha-methyl -5alpha-ergost - 8-enol and 2,4- 3H- 5 alpha- ergosta-8, 14-dienol in chlorella ellipsoidea.

6. Metabolism of 2,4-3H-14alpha-methyl-5alpha-ergost-8-enol and 2,4-3H-5alpha-ergosta-8,14-dienol in Ochromonas malhamensis.

7. The intermediary role of a steroid 8,14-dien-3-beta-ol system in ergosterol biosynthesis.

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