Glycerol backbone conformation in phosphatidylcholines is primarily determined by the intramolecular stacking of the vicinally arranged acyl chains.

Arora, A and Gupta, C M (1997) Glycerol backbone conformation in phosphatidylcholines is primarily determined by the intramolecular stacking of the vicinally arranged acyl chains. Biochimica et biophysica acta, 1324 (1). pp. 47-60. ISSN 0006-3002

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Abstract

To analyse the effect of the altered glycerol backbone structure on the glycerophospholipid conformation, we have replaced the glycerol moiety by the rac-1,2,4-butanetriol residue in 1,2-diacyl-sn-glycero-3-phosphocholines (PC), and then analysed the resulting 1,2-dialkanoyloxy-rac-but-4-yl-[2-(trimethylammonium)ethyl] phosphates (1,2-bPC) and 1,3-dial-kanoyloxy-rac-but-4-yl-[2-(trimethylammonium)ethyl] phosphates (1,3-bPC) by high-resolution 1H- and 13C-NMR spectroscopy in both CDCI3 and D2O. The preferred conformation about the C1-C2 glycerol bond in PC was almost completely preserved in 1,2-bPC, but it was completely random in case of 1,3-bPC. Out of the three C-C bonds present in the butanetriol backbone of 1,3-bPC, only the C2-C3 bond experienced a restricted rotation. However, the conformational preference about this bond was virtually similar to that observed for the C1-C2 bond in PC. These results clearly demonstrate that the preferred conformation of the glycerol backbone is determined primarily by the intramolecular acyl chain stacking which essentially requires a vicinal arrangement of the acyl chains in glycerophospholipids.

Item Type:	Article
Additional Information:	Copyright of this article belongs to Elsevier Science
Uncontrolled Keywords:	Phospholipid conformation; Glycerol backbone; Butanetriol analog; NMR; Micelle; Bilayer
Subjects:	Q Science > QD Chemistry
Depositing User:	Dr. K.P.S.Sengar
Date Deposited:	16 Dec 2011 08:56
Last Modified:	27 Mar 2014 09:31
URI:	http://crdd.osdd.net/open/id/eprint/372

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