Identification of C-24 alkyl epimers of marine sterols by 13C nuclear magnetic resonance spectroscopy
Authors:
- J. L. C. SrightJSJ. L. C. Sright
- A. G. McInnesAMA. G. McInnes
- S. ShimizuSSS. Shimizu
- D. G. SmithDSD. G. Smith
- J. A. WalterJWJ. A. Walter
- D. IdlerDID. Idler
- W. KhalilWKW. Khalil
- 15 July 1978
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 56 (14) , 1898-1903
Abstract
13C 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 1H 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.Keywords
This publication has 2 references indexed in Scilit:
- Carbon-13 NMR studies on cholesterol biosynthesized from [13C]mevalonatesJournal of the American Chemical Society, 1977
- The occurrence of C29 sterols with different configurations at C-24 in Cucurbita Pepo as shown by 270 MHz NMRPhytochemistry, 1976