Stereochemistry of sterol biosynthesis: Interrelationship of the terminal methyl groups in squalene, the C-1,1′ methyls in squalene 2,3-oxide, and the C-30,31 methyls in lanosterol

K. J. Stone; W. R. Roeske; R. B. Clayton; E. E. Van Tamelen

doi:10.1039/C29690000530

Stereochemistry of sterol biosynthesis: Interrelationship of the terminal methyl groups in squalene, the C-1,1′ methyls in squalene 2,3-oxide, and the C-30,31 methyls in lanosterol

K. J. Stone
, W. R. Roeske
, R. B. Clayton
, E. E. Van Tamelen

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

The trans-terminal methyls of squalene derive from C-2 of mevalonic acid, and the conversion of squalene in turn into squalene 2,3-oxide and lanosterol occurs without interchange of isopropylidene methyls, so that C-2 of mevalonic acid provides the 4α-methyl group of lanosterol.

Original language	English (US)
Pages (from-to)	530-532
Number of pages	3
Journal	Journal of the Chemical Society D: Chemical Communications
Issue number	10
DOIs	https://doi.org/10.1039/C29690000530
State	Published - 1969
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

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10.1039/C29690000530

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Stereochemistry of sterol biosynthesis: Interrelationship of the terminal methyl groups in squalene, the C-1,1′ methyls in squalene 2,3-oxide, and the C-30,31 methyls in lanosterol. / Stone, K. J.; Roeske, W. R.; Clayton, R. B. et al.
In: Journal of the Chemical Society D: Chemical Communications, No. 10, 1969, p. 530-532.

Research output: Contribution to journal › Article › peer-review

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title = "Stereochemistry of sterol biosynthesis: Interrelationship of the terminal methyl groups in squalene, the C-1,1′ methyls in squalene 2,3-oxide, and the C-30,31 methyls in lanosterol",

abstract = "The trans-terminal methyls of squalene derive from C-2 of mevalonic acid, and the conversion of squalene in turn into squalene 2,3-oxide and lanosterol occurs without interchange of isopropylidene methyls, so that C-2 of mevalonic acid provides the 4α-methyl group of lanosterol.",

author = "Stone, \{K. J.\} and Roeske, \{W. R.\} and Clayton, \{R. B.\} and \{Van Tamelen\}, \{E. E.\}",

note = "Funding Information: These studies were discussed, or the possibility that the first-formed carbonium supported by a grant from the U.S.P.H.S. (to E. E. v. T.), ion is prevented from rotation by a specific interaction with by a grant-in-aid from the American Heart Association (to the enzyme active site.",

year = "1969",

doi = "10.1039/C29690000530",

language = "English (US)",

pages = "530--532",

journal = "Journal of the Chemical Society D: Chemical Communications",

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T2 - Interrelationship of the terminal methyl groups in squalene, the C-1,1′ methyls in squalene 2,3-oxide, and the C-30,31 methyls in lanosterol

AU - Stone, K. J.

AU - Roeske, W. R.

AU - Clayton, R. B.

AU - Van Tamelen, E. E.

N1 - Funding Information: These studies were discussed, or the possibility that the first-formed carbonium supported by a grant from the U.S.P.H.S. (to E. E. v. T.), ion is prevented from rotation by a specific interaction with by a grant-in-aid from the American Heart Association (to the enzyme active site.

PY - 1969

Y1 - 1969

N2 - The trans-terminal methyls of squalene derive from C-2 of mevalonic acid, and the conversion of squalene in turn into squalene 2,3-oxide and lanosterol occurs without interchange of isopropylidene methyls, so that C-2 of mevalonic acid provides the 4α-methyl group of lanosterol.

AB - The trans-terminal methyls of squalene derive from C-2 of mevalonic acid, and the conversion of squalene in turn into squalene 2,3-oxide and lanosterol occurs without interchange of isopropylidene methyls, so that C-2 of mevalonic acid provides the 4α-methyl group of lanosterol.

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JO - Journal of the Chemical Society D: Chemical Communications

JF - Journal of the Chemical Society D: Chemical Communications

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ER -

Stereochemistry of sterol biosynthesis: Interrelationship of the terminal methyl groups in squalene, the C-1,1′ methyls in squalene 2,3-oxide, and the C-30,31 methyls in lanosterol

Abstract

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