Efficient and green aqueous−solid system for transphosphatidylation to produce phosphatidylhydroxybutyrate: Potential drugs for central nervous system's diseases

Abstract

The synthesis of nonnatural phospholipid, phosphatidylhydroxybutyrate (PB), was firstly introduced by phospholipase D (PLD)‐mediated transphosphatidylation of phosphatidylcholine (PC) with sodium γ‐hydroxybutyrate (NaGHB) in the aqueous–solid system. Nanoscale silicon dioxide (NSD) was employed as a carrier to provide an “artificial interphase” between PC and PLD. Special attention has been paid to the effect of the PC coverage on the surface area of hybrids of NSD‐PC, the PC loading and the yield of PB. Results indicated that the highest PC loading of 98.3% and the highest PB yield of 97.3% were achieved. In addition, the free PLD in the aqueous–solid system showed the greater stability and pH tolerance than that in the traditional liquid–liquid system. The operational stability of free PLD solution was investigated. The yield of PB remained 70.7% after being used for five batches. The authors provide a new idea for drug design and the potential source of PB for medical experiments. PB is a potential drug and may have the excellent performance in the treatment of central nervous system's diseases. © 2018 American Institute of Chemical Engineers Biotechnol. Prog., 35: e2726, 2019

Efficient immobilized phospholipase A1 on Mo‐basing nanomaterials for enzymatic degumming

“…It has both negatively charged phosphoryl group and positively charged choline group. The choline group located on the terminal of PC polar group, which had lower steric resistance and might be more available to interact with the outer surface of nanoparticles 28–30 . Thus, the strong repulsion among positive charges might not be beneficial for the adsorption of PC.…”

“…The choline group located on the terminal of PC polar group, which had lower steric resistance and might be more available to interact with the outer surface of nanoparticles. [28][29][30] Thus, the strong repulsion among positive charges might not be beneficial for the adsorption of PC. Our previous studies also supported this point that the amphipathic PC molecule would like to adsorb on the suitable support surface, which is neither extremely hydrophilic nor hydrophobic.…”

Polar Head Modified Phospholipids by Phospholipase D-Catalyzed Transformations of Natural Phosphatidylcholine for Targeted Applications: An Overview

“…Very recently, in 2019, Li et al described the preparation of a novel PL, phosphatidylhydroxybutyrate (PB, PX-21), for the application in the field of anesthetic and sedatives [88]. The new PL, was prepared by transphosphatidylation of PC with sodium γ-hydroxybutyrate (NaGHB, as shown in Scheme 12).…”

Phospholipid metabolites of GHB as potential biomarkers in whole blood: Synthesis, analytics, and in vitro formation of homolog 16:0/18:1

“…In a recent study by Krämer et al, the fatty acid ester palmitoyloxy butyrate was synthesized as a reference compound and identified in an authentic plasma sample 27 . Phospholipids, like the PEth homologs, are formed by phospholipase D (PLD) in the presence of phosphatidylcholines (PC) and ethanol 28–31 . For PEth, 48 homologs were found in an authentic blood sample, and PEth 16:0/18:1 was identified as the most abundant homolog 32–35 .…”

“…27 Phospholipids, like the PEth homologs, are formed by phospholipase D (PLD) in the presence of phosphatidylcholines (PC) and ethanol. [28][29][30][31] For PEth, 48 homologs were found in an authentic blood sample, and PEth 16:0/18:1 was identified as the most abundant homolog. [32][33][34][35] But PLD also exhibits a high affinity for other shortchain alcohols, and GHB is described as a substrate.…”