Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor. (September 2020)

• Record Type: Journal Article
• Authors: Struzik, Zachary J.; Weerts, Ashley N.; Storch, Judith; Thompson, David H.
• Is Part Of: Chemistry and physics of lipids. Volume 231(2020)
• Publication Date: 2020-09
• Subjects: PG Phosphatidyl glycerols -- BMP Bis(monoacylglycerolphosphate) -- PMB p-methoxybenzylether -- DAG Diacylglycerol -- DMF Dimethylformamide -- DCM Dichloromethane -- THF Tetrahydrofuran -- MeOH Methanol -- t-BuOOH tert-Butylhydroperoxide -- EtOAc Ethyl acetate -- AcOH Acetic acid -- TBAF Tetra-n-butylammonium fluoride -- DCC N, N'-Dicyclohexylcarbodiimide -- TBS tert-Butyldimethylsilylether -- DDQ 2, 3-Dichloro-5, 6-dicyano-1, 4-benzoquinone -- MeCN Acetonitrile -- DMAP 4-Dimethylaminopyridine -- TMS Tetramethylsilylether -- PNN 2-cyanoethyl N, N, N′, N′-tetraisopropylphosphorodiamidite -- PNCl N, Ndiisopropylchlorophosphoramidite; Stereospecific synthesis -- Phosphatidylglycerol -- Phosphoramidite methodology -- Dioleoyl glycerophospholipid; Lipids -- Periodicals; Lipids -- Periodicals; Lipides -- Périodiques; Lipids; Periodicals; Electronic journals; 547.77
• DOI: 10.1016/j.chemphyslip.2020.104933
• Languages: English
• ISSNs: 0009-3084

Abstract

Graphical abstract: Highlights: A synthetic route to provide control over the PG stereocenters from solketal precursors. Approach potentially enables control over acyl chain identity. Acyl chain migration avoided by careful control over reaction time and conditions. Phosphoglycerol headgroup introduced using phosphoramidite intermediate. Abstract: Phosphatidylglycerols (PG) are a family of naturally occurring phospholipids that are responsible for critical operations within cells. PG are characterized by an ( R ) configuration in the diacyl glycerol backbone and an ( S ) configuration in the phosphoglycerol head group. Herein, we report a synthetic route to provide control over the PG stereocenters as well as control of the acyl chain identity.