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A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates

A sustainable and green approach was developed for the scalable synthesis of uncommon naturally occurring phospholipid species, Hemi-bis(monoacylglycero)phosphates (Hemi-BMPs) and bis(diacylglycero)phosphates (BDPs) via the phospholipase D (PLD) mediated transphosphatidylation. PLD from Streptomyces...

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Detalles Bibliográficos
Autores principales: Bogojevic, Oliver, Zhang, Yan, Wolff, Christian Daugaard, Nygaard, Jens Vinge, Wiking, Lars, Arevång, Carl, Guo, Zheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10336169/
https://www.ncbi.nlm.nih.gov/pubmed/37448559
http://dx.doi.org/10.1016/j.isci.2023.107075
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author Bogojevic, Oliver
Zhang, Yan
Wolff, Christian Daugaard
Nygaard, Jens Vinge
Wiking, Lars
Arevång, Carl
Guo, Zheng
author_facet Bogojevic, Oliver
Zhang, Yan
Wolff, Christian Daugaard
Nygaard, Jens Vinge
Wiking, Lars
Arevång, Carl
Guo, Zheng
author_sort Bogojevic, Oliver
collection PubMed
description A sustainable and green approach was developed for the scalable synthesis of uncommon naturally occurring phospholipid species, Hemi-bis(monoacylglycero)phosphates (Hemi-BMPs) and bis(diacylglycero)phosphates (BDPs) via the phospholipase D (PLD) mediated transphosphatidylation. PLD from Streptomyces sp. showed great substrate promiscuity for both phospholipids from different biological sources, and alcohol donors with diverse regiochemistry; monoacylglycerols with diverse fatty acyl structures (C12-C22), affording 74–92 wt% yields in 2 h. Experimental results demonstrated that the reaction rate is rather independent of phosphatidyls but to a large extent governed by the size, shape and regiolocation of fatty acyls incorporated on the glycerol backbone, particularly for the regio-isomers of bulky diacylglycerols (Sn-1,3 or Sn-1,2), which displays great diversity. In addition, a plausible mechanism is proposed based on molecular simulations for an elaborated explanation of the reaction thermodynamic and kinetic favorability toward the synthesis of Hemi-BMPs and BDPs.
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spelling pubmed-103361692023-07-13 A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates Bogojevic, Oliver Zhang, Yan Wolff, Christian Daugaard Nygaard, Jens Vinge Wiking, Lars Arevång, Carl Guo, Zheng iScience Article A sustainable and green approach was developed for the scalable synthesis of uncommon naturally occurring phospholipid species, Hemi-bis(monoacylglycero)phosphates (Hemi-BMPs) and bis(diacylglycero)phosphates (BDPs) via the phospholipase D (PLD) mediated transphosphatidylation. PLD from Streptomyces sp. showed great substrate promiscuity for both phospholipids from different biological sources, and alcohol donors with diverse regiochemistry; monoacylglycerols with diverse fatty acyl structures (C12-C22), affording 74–92 wt% yields in 2 h. Experimental results demonstrated that the reaction rate is rather independent of phosphatidyls but to a large extent governed by the size, shape and regiolocation of fatty acyls incorporated on the glycerol backbone, particularly for the regio-isomers of bulky diacylglycerols (Sn-1,3 or Sn-1,2), which displays great diversity. In addition, a plausible mechanism is proposed based on molecular simulations for an elaborated explanation of the reaction thermodynamic and kinetic favorability toward the synthesis of Hemi-BMPs and BDPs. Elsevier 2023-06-09 /pmc/articles/PMC10336169/ /pubmed/37448559 http://dx.doi.org/10.1016/j.isci.2023.107075 Text en © 2023 The Author(s) https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Bogojevic, Oliver
Zhang, Yan
Wolff, Christian Daugaard
Nygaard, Jens Vinge
Wiking, Lars
Arevång, Carl
Guo, Zheng
A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates
title A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates
title_full A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates
title_fullStr A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates
title_full_unstemmed A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates
title_short A sustainable and regioselective synthesis of Hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates
title_sort sustainable and regioselective synthesis of hemi-bis(monoacylglycero)phosphates and bis(diacylglycero)phosphates
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10336169/
https://www.ncbi.nlm.nih.gov/pubmed/37448559
http://dx.doi.org/10.1016/j.isci.2023.107075
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