Identification of C-24 alkyl epimers of marine sterols by ¹³C nuclear magnetic resonance spectroscopy

Abstract

13 C nuclear magnetic resonance spectra of diastereomeric C-24 alkyl sterols have been assigned. Differences in the chemical shifts of side-chain carbons permitted the determination of the absolute configuration at C-24 in several sterols since these chemical shifts are insensitive to structural changes remote from the asymmetric centre. An unknown sterol from Tetraselmissuecica has been identified as (24R)-24-methylcholest-5-en-3β-ol and the configuration assigned from 1 H nmr data to the sterol from Phaeodoctylumtricornutum has been confirmed. The utility and potential of this method in characterising new sterols and their biological precursors is discussed.