Production of specifically deuterium labelled dioleoyl phospholipid species in gram quantities: A convenient synthesis of [C[11-2H2]oleic acid
✍ Scribed by S.B. Farren; E. Sommerman; P.R. Cullis
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- English
- Weight
- 380 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0009-3084
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✦ Synopsis
A relatively straightforward large scale (gram quantity) synthesis of oleic acid specifically labelled with deuterium (2H) at the 11 position ([C11-:H2]oleic acid) is described. This synthesis is a modified version of the procedure of Tucker et al. (J. Labelled Compd., 7(1971)137) and involves the coupling of [C2-2H2] nonanal with methyl 9-chlorononanoate via a Wittig reaction. The 2H-labelled nonanal is produced in greater than 75% yield. The coupling reaction results in a 60-70% yield (based on the aldehyde) which contains 95% of the cis (oleic acid) isomer. The subsequent synthesis of 1,2-[C11-2H2] dioleoyl-sn-glycero-3-phosphorylcholine ([Cll-2H2]DOPC) yields a compound which exhibits a convenient 2H-NMR quadrupolar splitting (-6 KHz at 20°C). Similarly labelled dioleoyl species of phosphatidylethanolamine (PE), phosphatidylserine (PS), phosphatidylglycerol (PG) and phosphatidic acid (PA) are easily derived from the [Cll-2H2]DOPC. The dioleoyl phosphatidylethanolamine ([CII-2H2]DOPE) shows similar bilayer to hexagonal (Hll) transition characteristics as unlabelled DOPE, and this transition can be conveniently monitored by 2H-NMR techniques.