Literature DB >> 17485208

Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2.

Chris M McGinley1, Cyril Jacquot, Wilfred A van der Donk.   

Abstract

The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G(2), creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection.

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Year:  2007        PMID： 17485208      PMCID： PMC2040112          DOI： 10.1016/j.bmcl.2007.04.073

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  25 in total

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Authors:  Carol A Rouzer; Lawrence J Marnett
Journal:  Chem Rev       Date:  2003-06       Impact factor: 60.622

2.  Inhibition of lysine 2,3-aminomutase by the alternative substrate 4-thialysine and characterization of the 4-thialysyl radical intermediate.

Authors:  J Miller; V Bandarian; G H Reed; P A Frey
Journal:  Arch Biochem Biophys       Date:  2001-03-15       Impact factor: 4.013

3.  Stereospecificity of hydrogen abstraction in the conversion of arachidonic acid to 15R-HETE by aspirin-treated cyclooxygenase-2. Implications for the alignment of substrate in the active site.

Authors:  C Schneider; A R Brash
Journal:  J Biol Chem       Date:  2000-02-18       Impact factor: 5.157

4.  Characterization of an allylic analogue of the 5'-deoxyadenosyl radical: an intermediate in the reaction of lysine 2,3-aminomutase.

Authors:  O T Magnusson; G H Reed; P A Frey
Journal:  Biochemistry       Date:  2001-07-03       Impact factor: 3.162

5.  Lysine 2,3-aminomutase and trans-4,5-dehydrolysine: characterization of an allylic analogue of a substrate-based radical in the catalytic mechanism.

Authors:  W Wu; S Booker; K W Lieder; V Bandarian; G H Reed; P A Frey
Journal:  Biochemistry       Date:  2000-08-08       Impact factor: 3.162

6.  Control of prostaglandin stereochemistry at the 15-carbon by cyclooxygenases-1 and -2. A critical role for serine 530 and valine 349.

Authors:  Claus Schneider; William E Boeglin; Jeffery J Prusakiewicz; Scott W Rowlinson; Lawrence J Marnett; Nigulas Samel; Alan R Brash
Journal:  J Biol Chem       Date:  2001-10-24       Impact factor: 5.157

7.  Structural characterization of arachidonyl radicals formed by aspirin-treated prostaglandin H synthase-2.

Authors:  Ah-lim Tsai; Graham Palmer; Gang Wu; Sheng Peng; Nicole M Okeley; Wilfred A van der Donk; Richard J Kulmacz
Journal:  J Biol Chem       Date:  2002-08-06       Impact factor: 5.157

8.  Synthesis of isotopically labeled arachidonic acids to probe the reaction mechanism of prostaglandin H synthase.

Authors:  Sheng Peng; Nicole M Okeley; Ah-Lim Tsai; Gang Wu; Richard J Kulmacz; Wilfred A van der Donk
Journal:  J Am Chem Soc       Date:  2002-09-11       Impact factor: 15.419

9.  Identification of a pharmacologically distinct prostaglandin H synthase in cultured epithelial cells.

Authors:  M J Holtzman; J Turk; L P Shornick
Journal:  J Biol Chem       Date:  1992-10-25       Impact factor: 5.157

10.  Spectroscopic evidence for reaction of prostaglandin H synthase-1 tyrosyl radical with arachidonic acid.

Authors:  A Tsai; R J Kulmacz; G Palmer
Journal:  J Biol Chem       Date:  1995-05-05       Impact factor: 5.157
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  3 in total

1.  3-Aminoazetidin-2-one derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors suitable for systemic administration.

Authors:  Annalisa Fiasella; Andrea Nuzzi; Maria Summa; Andrea Armirotti; Glauco Tarozzo; Giorgio Tarzia; Marco Mor; Fabio Bertozzi; Tiziano Bandiera; Daniele Piomelli
Journal:  ChemMedChem       Date:  2014-05-14       Impact factor: 3.466

Review 2.  Prostaglandin H synthase: resolved and unresolved mechanistic issues.

Authors:  Ah-Lim Tsai; Richard J Kulmacz
Journal:  Arch Biochem Biophys       Date:  2009-09-01       Impact factor: 4.013

3.  Synthesis of 11-thialinoleic acid and 14-thialinoleic acid, inhibitors of soybean and human lipoxygenases.

Authors:  Cyril Jacquot; Chris M McGinley; Erik Plata; Theodore R Holman; Wilfred A van der Donk
Journal:  Org Biomol Chem       Date:  2008-09-30       Impact factor: 3.876
  3 in total

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