Literature DB >> 22822273

Application of Chemoenzymatic Hydrolysis in the Synthesis of 2-Monoacylglycerols.

Kyle M Whitten1, Alexandros Makriyannis, Subramanian K Vadivel.   

Abstract

The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized Candida antarctica within 2h with yields ranging from 36%-83%. Similar reaction conditions with immobilized Rhizomucor miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.

Entities:  

Year:  2012        PMID: 22822273      PMCID: PMC3398708          DOI: 10.1016/j.tet.2012.04.101

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  15 in total

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Authors:  Didier M Lambert; Christopher J Fowler
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446

2.  A methodology for radiolabeling of the endocannabinoid 2-arachidonoylglycerol (2-AG).

Authors:  Richard I Duclos; Meghan Johnston; Subramanian K Vadivel; Alexandros Makriyannis; Sherrye T Glaser; S John Gatley
Journal:  J Org Chem       Date:  2011-03-03       Impact factor: 4.354

3.  Chemoenzymatic Synthesis of 2-Arachidonoylglycerol, An Endogenous Ligand for Cannabinoid Receptors.

Authors:  Subramanian K Vadivel; Kyle M Whitten; A Makriyannis
Journal:  Tetrahedron Lett       Date:  2011-03-16       Impact factor: 2.415

4.  High affinity electrophilic and photoactivatable covalent endocannabinoid probes for the CB1 receptor.

Authors:  Chen Li; Wei Xu; Subramanian K Vadivel; Pusheng Fan; Alexandros Makriyannis
Journal:  J Med Chem       Date:  2005-10-06       Impact factor: 7.446

5.  Highly selective synthesis of 1,3-oleoyl-2-palmitoylglycerol by lipase catalysis.

Authors:  U Schmid; U T Bornscheuer; M M Soumanou; G P McNeill; R D Schmid
Journal:  Biotechnol Bioeng       Date:  1999-09-20       Impact factor: 4.530

Review 6.  The medicinal chemistry of agents targeting monoacylglycerol lipase.

Authors:  Alma Viso; José A Cisneros; Silvia Ortega-Gutiérrez
Journal:  Curr Top Med Chem       Date:  2008       Impact factor: 3.295

Review 7.  The complex and important cellular and metabolic functions of saturated fatty acids.

Authors:  Philippe Legrand; Vincent Rioux
Journal:  Lipids       Date:  2010-07-13       Impact factor: 1.880

8.  Intestinal absorption and lymphatic transport of eicosapentaenoic (EPA), docosahexaenoic (DHA), and decanoic acids: dependence on intramolecular triacylglycerol structure.

Authors:  M S Christensen; C E Høy; C C Becker; T G Redgrave
Journal:  Am J Clin Nutr       Date:  1995-01       Impact factor: 7.045

9.  Analysis of endocannabinoids by Ag+ coordination tandem mass spectrometry.

Authors:  Philip J Kingsley; Lawrence J Marnett
Journal:  Anal Biochem       Date:  2003-03-01       Impact factor: 3.365

10.  Development of novel tail-modified anandamide analogs.

Authors:  Fenmei Yao; Chen Li; Subramanian K Vadivel; Anna L Bowman; Alexandros Makriyannis
Journal:  Bioorg Med Chem Lett       Date:  2008-07-31       Impact factor: 2.823

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  2 in total

1.  Design and synthesis of novel prostaglandin E2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s).

Authors:  Erin L Shelnut; Spyros P Nikas; David F Finnegan; Nan Chiang; Charles N Serhan; Alexandros Makriyannis
Journal:  Tetrahedron Lett       Date:  2015-03-11       Impact factor: 2.415

2.  2-Arachidonoylglycerol Synthesis: Facile and Handy Enzymatic Method That Allows to Avoid Isomerization.

Authors:  Roberta Ottria; Silvana Casati; Paola Rota; Pierangela Ciuffreda
Journal:  Molecules       Date:  2022-08-15       Impact factor: 4.927

  2 in total

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