AI Article Synopsis
- BMP is a potential biomarker for drug-induced phospholipidosis (DIPL), prompting the need for both unlabelled and stable isotope labelled versions as internal standards.
- The synthesis process of BMP involved converting isopropylideneglycerol to a specific glycerol derivative in three steps, initially using an ineffective protecting group that led to compound decomposition.
- By changing to a more suitable protecting group, the synthesis was successfully completed, allowing for the production of both BMP and its isotope-labeled version.
Article Abstract
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 [ C ]BMP from [ C ]glycerol.
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Article Synopsis
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- By changing to a more suitable protecting group, the synthesis was successfully completed, allowing for the production of both BMP and its isotope-labeled version.
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