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

J. L. C. Sright | Zendy; A. G. McInnes | Zendy; Susana Shimizu | Zendy; Donald G. Smith | Zendy; John A. Walter | Zendy; D. R. Idler | Zendy; Wagdy K. B. Khalil | Zendy

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

Author(s) -

J. L. C. Sright,

A. G. McInnes,

Susana Shimizu,

Donald G. Smith,

John A. Walter,

D. R. Idler,

Wagdy K. B. Khalil

Publication year - 1978

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v78-308

Subject(s) - chemistry , diastereomer , epimer , sterol , chemical shift , alkyl , nuclear magnetic resonance spectroscopy , side chain , stereochemistry , absolute configuration , two dimensional nuclear magnetic resonance spectroscopy , spectroscopy , ergosterol , nuclear magnetic resonance , organic chemistry , biochemistry , cholesterol , physics , quantum mechanics , polymer

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.

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