A practical selective synthesis of mixed short/long chains glycerophosphocholines.
Glycerophosphorylcholine (GPC) is transformed into the cyclic stannylene derivatives, which are selectively acylated to 1-acyl-2-lyso-glycerophosphocholines. The reaction is effective using C-2 to C-16 acid chlorides in 2-propanol. After solvent replacement the lyso-phospholipid (lyso-PL) is subjected to a second acylation using acid anhydrides in methylene chloride. A series of 1(2)-short-2(1)-long-diacyl-glycerophosphocholines are obtained in high yields and selectivity. No diacylation product was detected. In order to detect mixed-chain lipids with inverted disposition of acyl chains, the long chain was introduced first and the thus resulting isomeric compounds compared by NMR. An NMR method was developed in order to determine the positional purity of the isomeric compounds.
D'Arrigo
Paola
P
Dipartimento di Chimica, Materiali e Ingegneria Chimica G. Natta, Politecnico di Milano, via Mancinelli 7, 20131 Milano, Italy. paola.d'arrigo@polimi.it
Fasoli
Ezio
E
Pedrocchi-Fantoni
Giuseppe
G
Rossi
Cristina
C
Saraceno
Caterina
C
Tessaro
Davide
D
Servi
Stefano
S
D002851:Chromatography, High Pressure Liquid; D005997:Glycerylphosphorylcholine / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010741:Phospholipases A / Q000378:metabolism
D005997:Glycerylphosphorylcholine; D010741:Phospholipases A