Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 175-181 |
| Number of pages | 6 |
| Journal | Chemistry and Physics of Lipids |
| Volume | 58 |
| Issue number | 1-2 |
| Publication status | Published - May 1991 |
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Keywords
- F-19-NMR
- H-2-NMR
- fluorosterols
- HDL
- DMPC-D54
- nuclear magnetic resonance
- cholesterol
- metabolism
- molecules
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A f-19 and deuterium nmr-study of two novel fluorosterols and their properties in model membranes and high-density-lipoprotein. / Reid, David G.; MacLachlan, L.K.; Suckling, K.E.; Gee, A.; Cresswell, S.; Suckling, C.J.
In: Chemistry and Physics of Lipids, Vol. 58, No. 1-2, 05.1991, p. 175-181.Research output: Contribution to journal › Article
TY - JOUR
T1 - A f-19 and deuterium nmr-study of two novel fluorosterols and their properties in model membranes and high-density-lipoprotein
AU - Reid, David G.
AU - MacLachlan, L.K.
AU - Suckling, K.E.
AU - Gee, A.
AU - Cresswell, S.
AU - Suckling, C.J.
PY - 1991/5
Y1 - 1991/5
N2 - 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.
AB - 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.
KW - F-19-NMR
KW - H-2-NMR
KW - fluorosterols
KW - HDL
KW - DMPC-D54
KW - nuclear magnetic resonance
KW - cholesterol
KW - metabolism
KW - molecules
UR - http://www.chem.strath.ac.uk/people/academic/sarah_l_cresswell/publications
M3 - Article
VL - 58
SP - 175
EP - 181
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
SN - 0009-3084
IS - 1-2
ER -