《751_ftp》.pdf

FULL PAPER DOI: 10.1002/ejoc.201001264 Synthesis of Trifunctional Phosphatidylserine Probes for Identification of Lipid-Binding Proteins Saibal Bandyopadhyay[a] and Dennis Bong*[a] Keywords: Lipids / Sensors / Receptors / Proteins / Synthesis design Phosphatidylserine (PS) lipids play a number of roles in cell headgroup for recognition, a benzophenone moiety for pho- biology, one of which is to mark apoptotic cells for clearance toaffinity cross-linking, and an alkyne for post-labeling read- by macrophages. PS recognition triggers macrophage re- out. These probes may be useful tools to identify new PS re- cognition and clearance, which occurs concomitantly with ceptors (PSRs). The PS lipid probes thus have potential im- active suppression of an inflammatory response. A small pact in the areas of discovery biology, anti-inflammatory number of proteins in different tissues have been identified therapeutics, and cellular delivery. We present herein a ver- as PS receptors, and we hypothesize that many more PS re- satile and robust synthetic approach to trifunctional phos- ceptors have yet to be found. We have designed and synthe- phatidyl serine lipid mimics for identification of novel PSR sized a set of phosphatidylserine lipid mimics with a PS lipid proteins. Introduction process, as only a handful of mutually exclusive receptors have been found in different cell lines. Phosphatidylserine Engulf