Strathprints Home | Open Access | Browse | Search | User area | Copyright | Help | Library Home | SUPrimo

A f-19 and deuterium nmr-study of two novel fluorosterols and their properties in model membranes and high-density-lipoprotein

Reid, David G. and MacLachlan, L.K. and Suckling, K.E. and Gee, A. and Cresswell, S. and Suckling, C.J. (1991) A f-19 and deuterium nmr-study of two novel fluorosterols and their properties in model membranes and high-density-lipoprotein. Chemistry and Physics of Lipids, 58 (1-2). pp. 175-181. ISSN 0009-3084

Full text not available in this repository. (Request a copy from the Strathclyde author)

Abstract

Fluorine-19 nuclear magnetic resonance at 235 MHz has been used to characterize the NMR properties of two novel fluorinated sterols, 6,6-difluorocholestanol and 7,7-difluorocholestanol, and various 3-ester derivatives. F-19-F-19 and F-19-H-1 coupling constants in chloroform are reported. H-2-NMR studies of side-chain perdeuterated dimyristoylphosphatidylcholine (DMPC-d54) prove that the two unesterified fluorosterols affect model membrane dynamical properties in a manner analogous to cholesterol. In aqueous detergent the F-19 chemical shifts of both 6,6- and 7,7-difluorocholestanols are perturbed about 1 ppm upfield by esterification at the 3-position, suggesting that F-19-NMR may be a useful monitor of enzyme catalyzed sterol acylation in vitro. Finally 6,6-difluorocholestanol oleate has been incorporated into human high density lipoprotein (HDL) and its F-19 signals observed in this environment. The appearance of the spectrum, and the results of lipophilic relaxation probe experiments, indicate that the acyl sterol partitions into at least two environments, and exhibits slightly different chemical shift and homonuclear scalar coupling characteristics in each.

Item type: Article
ID code: 16783
Keywords: F-19-NMR, H-2-NMR, fluorosterols, HDL, DMPC-D54, nuclear magnetic resonance, cholesterol, metabolism, molecules, Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
Depositing user: Strathprints Administrator
Date Deposited: 19 Mar 2010 15:32
Last modified: 04 Oct 2012 12:54
URI: http://strathprints.strath.ac.uk/id/eprint/16783

Actions (login required)

View Item