Reduction of Δ24 of Lanosterol in the Biosynthesis of Cholesterol by Rat Liver Enzymes. II. Stereochemistry of Addition of the C-25 Proton

Marzia Galli Kienle; Ravi K. Varma; Lawrence J. Mulheirn; Boris Yagen; Eliahu Caspi

doi:10.1021/ja00787a046

Reduction of Δ²⁴ of Lanosterol in the Biosynthesis of Cholesterol by Rat Liver Enzymes. II. Stereochemistry of Addition of the C-25 Proton

Marzia Galli Kienle, Ravi K. Varma, Lawrence J. Mulheirn, Boris Yagen, Eliahu Caspi^*

^*Corresponding author for this work

School of Pharmacy

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23 Scopus citations

Abstract

Mycobacterium smegmatis converts cholesterol to (25S)-26-hydroxycholest-4-en-3-one. It was shown, with the use of [¹⁴C₅]cholesterol biosynthesized from [2-¹⁴C]mevalonic acid in the S-10 fraction of rat livers, that the 26-¹⁴C atom bore the oxygen atom. Evidence is provided that the 26-hydroxylation by M. smegmatis proceeds without loss of the C-25 hydrogen. Barring rearrangement and migration of this hydrogen, it may be inferred that the C-26-hydroxylation proceeds without epimerization at C-25. Previously, we demonstrated that in the reduction of Δ²⁴ of lanosterol a 24-pro-S hydrogen is added. It follows that the reduction of Δ²⁴ of lanosterol in the biosynthesis of cholesterol in the S-10 fraction of rat liver entails the overall cis addition of two hydrogen atoms.

Original language	English
Pages (from-to)	1996-2001
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	95
Issue number	6
DOIs	https://doi.org/10.1021/ja00787a046
State	Published - 1 Mar 1973

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title = "Reduction of Δ24 of Lanosterol in the Biosynthesis of Cholesterol by Rat Liver Enzymes. II. Stereochemistry of Addition of the C-25 Proton",

abstract = "Mycobacterium smegmatis converts cholesterol to (25S)-26-hydroxycholest-4-en-3-one. It was shown, with the use of [14C5]cholesterol biosynthesized from [2-14C]mevalonic acid in the S-10 fraction of rat livers, that the 26-14C atom bore the oxygen atom. Evidence is provided that the 26-hydroxylation by M. smegmatis proceeds without loss of the C-25 hydrogen. Barring rearrangement and migration of this hydrogen, it may be inferred that the C-26-hydroxylation proceeds without epimerization at C-25. Previously, we demonstrated that in the reduction of Δ24 of lanosterol a 24-pro-S hydrogen is added. It follows that the reduction of Δ24 of lanosterol in the biosynthesis of cholesterol in the S-10 fraction of rat liver entails the overall cis addition of two hydrogen atoms.",

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AU - Varma, Ravi K.

AU - Mulheirn, Lawrence J.

AU - Yagen, Boris

AU - Caspi, Eliahu

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N2 - Mycobacterium smegmatis converts cholesterol to (25S)-26-hydroxycholest-4-en-3-one. It was shown, with the use of [14C5]cholesterol biosynthesized from [2-14C]mevalonic acid in the S-10 fraction of rat livers, that the 26-14C atom bore the oxygen atom. Evidence is provided that the 26-hydroxylation by M. smegmatis proceeds without loss of the C-25 hydrogen. Barring rearrangement and migration of this hydrogen, it may be inferred that the C-26-hydroxylation proceeds without epimerization at C-25. Previously, we demonstrated that in the reduction of Δ24 of lanosterol a 24-pro-S hydrogen is added. It follows that the reduction of Δ24 of lanosterol in the biosynthesis of cholesterol in the S-10 fraction of rat liver entails the overall cis addition of two hydrogen atoms.

AB - Mycobacterium smegmatis converts cholesterol to (25S)-26-hydroxycholest-4-en-3-one. It was shown, with the use of [14C5]cholesterol biosynthesized from [2-14C]mevalonic acid in the S-10 fraction of rat livers, that the 26-14C atom bore the oxygen atom. Evidence is provided that the 26-hydroxylation by M. smegmatis proceeds without loss of the C-25 hydrogen. Barring rearrangement and migration of this hydrogen, it may be inferred that the C-26-hydroxylation proceeds without epimerization at C-25. Previously, we demonstrated that in the reduction of Δ24 of lanosterol a 24-pro-S hydrogen is added. It follows that the reduction of Δ24 of lanosterol in the biosynthesis of cholesterol in the S-10 fraction of rat liver entails the overall cis addition of two hydrogen atoms.

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Reduction of Δ²⁴ of Lanosterol in the Biosynthesis of Cholesterol by Rat Liver Enzymes. II. Stereochemistry of Addition of the C-25 Proton

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