Reduction of the 24,25-double bond of lanosterol in vivo in the rat. Stereochemistry of the addition of the C-25 proton in the biosynthesis of cholesterol

Boris Yagen, Joseph S. O'Grodnick, Eliahu Caspi*, Christoph Tamm

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The stereochemistry of addition of the 25-proton in the Δ24 reduction of lanosterol to cholesterol in vivo in the rat is shown to be the same as that in the S-10 fraction of rat liver homogenstes. It is also shown that oxidation of [1,2-3H2]octan-1-ol by the Pfitzner-Moffatt method proceeds with complete removal of tritium from C-2 of octanol. A similar oxidation of [25-3H]-5α-cholestane-3β,26-diol to 3-oxo[25-3H]-5α-cholestan-26-al resulted in the loss of 23% of tritium. In contrast, Collins oxidation of [1,2-3H2]octan-1-ol to octanal did not involve any loss of tritium from C-2.

Original languageEnglish
Pages (from-to)1994-2000
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
StatePublished - 1974
Externally publishedYes

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