Literature DB >> 32533981

Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor.

Zachary J Struzik1, Ashley N Weerts1, Judith Storch2, David H Thompson3.   

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.
Copyright © 2020 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  Dioleoyl glycerophospholipid; Phosphatidylglycerol; Phosphoramidite methodology; Stereospecific synthesis

Mesh：

Substances：

Year:  2020        PMID： 32533981      PMCID： PMC7484214          DOI： 10.1016/j.chemphyslip.2020.104933

Source DB:  PubMed          Journal:  Chem Phys Lipids        ISSN： 0009-3084            Impact factor:   3.329


  25 in total

1.  Piant phospholipids. I. Identification of the phosphatidyl glycerols.

Authors:  A A BENSON; B MARUO
Journal:  Biochim Biophys Acta       Date:  1958-01

2.  Concise synthesis of ether analogues of lysobisphosphatidic acid.

Authors:  Guowei Jiang; Yong Xu; Thomas Falguières; Jean Gruenberg; Glenn D Prestwich
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

3.  Practical enantiospecific syntheses of lysobisphosphatidic acid and its analogues.

Authors:  Guowei Jiang; Yong Xu; Glenn D Prestwich
Journal:  J Org Chem       Date:  2006-02-03       Impact factor: 4.354

4.  Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit.

Authors:  D Jamin Keith; Steven D Townsend
Journal:  J Am Chem Soc       Date:  2019-08-01       Impact factor: 15.419

5.  Synthesis of Phosphatidylserine and Its Stereoisomers: Their Role in Activation of Blood Coagulation.

Authors:  Suman Mallik; Ramesh Prasad; Anindita Bhattacharya; Prosenjit Sen
Journal:  ACS Med Chem Lett       Date:  2018-04-12       Impact factor: 4.345

Review 6.  Specific roles of phosphatidylglycerols in hosts and microbes.

Authors:  Isabelle Dugail; Brandon D Kayser; Marie Lhomme
Journal:  Biochimie       Date:  2017-05-05       Impact factor: 4.079

7.  Simple synthesis of diastereomerically pure phosphatidylglycerols by phospholipase D-catalyzed transphosphatidylation.

Authors:  Rina Sato; Yutaka Itabashi; Hironori Fujishima; Hidetoshi Okuyama; Arnis Kuksis
Journal:  Lipids       Date:  2004-10       Impact factor: 1.880

8.  The Lewis base-catalyzed silylation of alcohols--a mechanistic analysis.

Authors:  Pascal Patschinski; Cong Zhang; Hendrik Zipse
Journal:  J Org Chem       Date:  2014-08-11       Impact factor: 4.354

Review 9.  Synthesis of lysophospholipids.

Authors:  Paola D'Arrigo; Stefano Servi
Journal:  Molecules       Date:  2010-03-08       Impact factor: 4.411

Review 10.  Lipid and Lipid Raft Alteration in Aging and Neurodegenerative Diseases: A Window for the Development of New Biomarkers.

Authors:  Fátima Mesa-Herrera; Lucas Taoro-González; Catalina Valdés-Baizabal; Mario Diaz; Raquel Marín
Journal:  Int J Mol Sci       Date:  2019-08-04       Impact factor: 5.923
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  1 in total

1.  Synthesis of Phosphatidyl Glycerol Containing Unsymmetric Acyl Chains Using H-Phosphonate Methodology.

Authors:  Zachary J Struzik; Shruti Biyani; Tim Grotzer; Judith Storch; David H Thompson
Journal:  Molecules       Date:  2022-03-28       Impact factor: 4.411
  1 in total

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