Chemical and Enzymatic Approaches to Esters ofsn‐Glycero‐3‐Phosphoric Acid

Abstract

Esters of sn‐glycero‐3‐phosphoric acid (GPAE) are derivatives of glycerophospholipids in which both the fatty acid chains in sn‐1 and sn‐2 positions are removed. Phosphatidylcholine (PC), phosphatidylethanolamine (PE), phosphatidylinositol (PI), and phosphatidylserine (PS) are the most abundant glycerophospholipids in Nature. Their deacylated derivatives find application in many industrial sectors; for example, sn‐glycero‐3‐phosphocholine (GPC) is useful as a cognitive enhancer and as a food ingredient, whereas sn‐glycero‐3‐phosphoinositol (GPI) acts as a natural anti‐inflammatory agent. This minireview covers the state‐of‐the‐art of chemical and biocatalytic methods for the obtainment of these lipid‐derived components.

2‐O‐Acetyl‐3,4,5,6‐tetra‐O‐benzyl‐d‐myo‐inosityl diphenylphosphate: A new useful intermediate to inositol phosphate and phospholipids

“…Starting from 6, GPI might be simply prepared by treatment with a properly protected glycerol synthon, followed by removal of all protective groups. 2…”

“…It is worth noting that, to the best of our knowledge, no chemical synthesis of GPI and its phosphorylated derivatives has been reported to date. Starting from 6 , GPI might be simply prepared by treatment with a properly protected glycerol synthon, followed by removal of all protective groups 2 …”

“…myo ‐Inositol, or cis ‐1,2,3,5‐ trans ‐4,6‐cyclohexanehexol, is the most common isomeric form in nature that also uses at least five of the others ( scyllo ‐, epi ‐, neo ‐, D‐ chiro ‐, and muco ‐inositols) 3 . It constitutes the structural core of a group of important metabolites, that is, inositol phosphates and inositol phospholipids, that are involved in numerous important biological processes including cellular signal transduction, membrane transport, protein anchoring, and cytoskeletal regulation 1–4 . Specifically, phosphatidylinositols, which constitute approximately 1% of the phospholipids in cell membranes, are selectively phosphorylated by multiple kinases at the C‐3, C‐4 and C‐5 positions to generate a number of endogenous phosphatidylinositol phosphates which are in turn converted into various inositol phosphates differing for the phosphorylation pattern of the inositol ring 3,5 …”

“…The inositols are the nine stereoisomeric forms of cyclohexanehexol belonging to the class of cyclitols, that is, cycloalkanes in which three or more ring atoms are each substituted with one hydroxyl group. 1,2 myo-Inositol, or cis-1,2,3,5-trans-4,6-cyclohexanehexol, is the most common isomeric form in nature that also uses at least five of the others (scyllo-, epi-, neo-, D-chiro-, and muco-inositols). 3 It constitutes the structural core of a group of important metabolites, that is, inositol phosphates and inositol phospholipids, that are involved in numerous important biological processes including cellular signal transduction, membrane transport, protein anchoring, and cytoskeletal regulation.…”

“…3 It constitutes the structural core of a group of important metabolites, that is, inositol phosphates and inositol phospholipids, that are involved in numerous important biological processes including cellular signal transduction, membrane transport, protein anchoring, and cytoskeletal regulation. [1][2][3][4] Specifically, phosphatidylinositols, which constitute approximately 1% of the phospholipids in cell membranes, are selectively phosphorylated by multiple kinases at the C-3, C-4 and C-5 positions to generate a number of endogenous phosphatidylinositol phosphates which are in turn converted into various inositol phosphates differing for the phosphorylation pattern of the inositol ring. 3,5 Concentrations of inositol derivatives in biological systems are very low, thus strongly limiting their analytical detection and the isolation from natural sources in useful amounts to fully elucidate their physiological functions.…”