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

DIR@IMTECH: CSIR-Institute of Microbial Technology

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Title Glycerol backbone conformation in phosphatidylcholines is primarily determined by the intramolecular stacking of the vicinally arranged acyl chains.
 
Creator Arora, A
Gupta, C M
 
Subject QD Chemistry
 
Description 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.
 
Publisher Elsevier Science
 
Date 1997-02-21
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://crdd.osdd.net/open/372/1/Guptacm1997.1.pdf
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
 
Relation http://www.sciencedirect.com/science/article/pii/S0005273697856982
http://crdd.osdd.net/open/372/