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Synthesis of di‐docosahexaenoyl (C22:6)‐bis(monoacylglycerol) phosphate in unlabelled and C‐13 labelled forms for use as a biomarker of drug induced phospholipidosis
Author(s) -
Hickey Michael J.,
Lindqvist Johnny,
Ha Young Hwan,
Andersson Håkan,
Elmore Charles S.
Publication year - 2019
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3714
Subject(s) - monoacylglycerol lipase , chemistry , phospholipidosis , ether , phosphate , drug , combinatorial chemistry , organic chemistry , biochemistry , pharmacology , membrane , medicine , phospholipid , endocannabinoid system , receptor
Di‐docosahexaenoyl (C22:6)‐bis(monoacylglycerol) phosphate (BMP) has been identified as a promising biomarker for drug‐induced phospholipidosis (DIPL). Both unlabelled and stable isotope labelled versions of BMP were desired for use as internal standards. Isopropylideneglycerol was converted to 4‐methoxyphenyldiphenylmethyl‐3‐PMB‐glycerol in three steps. Initially, the 2‐postion of the glycerol was protected as a t ‐butyldiphenylsilyl ether, which proved to be a mistake; deprotection of the ether resulted in the decomposition of the compound. A switch to a t ‐butyldimethylsilyl ether protecting group resulted in an intermediate that could be deprotected to the alcohol to give the target compound after salt exchange. The same procedure was used to prepare [ 13 C 6 ]BMP from [ 13 C 3 ]glycerol.