Literature DB >> 32523235

Synthesis of tetranor-PGE1: a urinary metabolite of prostaglandins E1 and E2.

Jennifer R Kimbrough1, Somnath Jana2, Kwangho Kim1,2, Alexander Allweil1, John A Oates3, Ginger L Milne2,3, Gary A Sulikowski1,2,3.   

Abstract

Prostaglandin E2 is produced in response to inflammation, often associated with human disease. As prostaglandins are rapidly metabolized, quantification of end urinary metabolites depend on chemical synthesis of isotopically labeled standards to support metabolite quantification. A concise synthesis of tetranor-PGE1 is described including a late stage incorporation of an isotopically labeled side-chain.

Entities:  

Keywords:  Heck reaction; Prostaglandins; Synthesis strategy; Total Synthesis

Year:  2020        PMID： 32523235      PMCID： PMC7286543          DOI： 10.1016/j.tetlet.2020.151922

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  14 in total

1.  Identification and assay of tetranor-prostaglandin E1 in human urine.

Authors:  J A Oates; B J SweetmAN; K Gréene; B Samuelsson
Journal:  Anal Biochem       Date:  1976-08       Impact factor: 3.365

2.  On the metabolism of prostaglandins E 1 and E 2 in man.

Authors:  M Hamberg; B Samuelsson
Journal:  J Biol Chem       Date:  1971-11-25       Impact factor: 5.157

3.  The effect of HIV and HPV coinfection on cervical COX-2 expression and systemic prostaglandin E2 levels.

Authors:  Daniel W Fitzgerald; Karl Bezak; Oksana Ocheretina; Cynthia Riviere; Thomas C Wright; Ginger L Milne; Xi Kathy Zhou; Baoheng Du; Kotha Subbaramaiah; Erin Byrt; Matthew L Goodwin; Arash Rafii; Andrew J Dannenberg
Journal:  Cancer Prev Res (Phila)       Date:  2011-12-01

4.  An efficient synthesis of 3-hetero-13,14-dihydro prostaglandin F1alpha analogues.

Authors:  J Gu; M J Dirr; Y Wang; D L Soper; B De; J A Wos; C R Johnson
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

5.  Quantifications of the major urinary metabolite of the E prostaglandins by mass spectrometry: evaluation of the method's application to clinical studies.

Authors:  H W Seyberth; B J Sweetman; J C Frolich; J A Oates
Journal:  Prostaglandins       Date:  1976-02

6.  Quantification of the major urinary metabolite of PGE2 by a liquid chromatographic/mass spectrometric assay: determination of cyclooxygenase-specific PGE2 synthesis in healthy humans and those with lung cancer.

Authors:  Laine J Murphey; Myles K Williams; Stephanie C Sanchez; Loretta M Byrne; Ildiko Csiki; John A Oates; David H Johnson; Jason D Morrow
Journal:  Anal Biochem       Date:  2004-11-15       Impact factor: 3.365

7.  Preparation of the Major Urinary Metabolite of (-)-Prostaglandin E(2).

Authors:  Douglass F Taber; Peiming Gu
Journal:  Tetrahedron       Date:  2009-08-01       Impact factor: 2.457

8.  Urinary PGE-M: a promising cancer biomarker.

Authors:  Dingzhi Wang; Raymond N DuBois
Journal:  Cancer Prev Res (Phila)       Date:  2013-05-01

9.  Suzuki-Miyaura cross-coupling of potassium trifluoroboratohomoenolates.

Authors:  Gary A Molander; Daniel E Petrillo
Journal:  Org Lett       Date:  2008-04-08       Impact factor: 6.005

Review 10.  Beyond prostaglandins--chemistry and biology of cyclic oxygenated metabolites formed by free-radical pathways from polyunsaturated fatty acids.

Authors:  Ullrich Jahn; Jean-Marie Galano; Thierry Durand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
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  1 in total

1.  Effect of Dysglycemia on Urinary Lipid Mediator Profiles in Persons With Pulmonary Tuberculosis.

Authors:  María B Arriaga; Farina Karim; Artur T L Queiroz; Mariana Araújo-Pereira; Beatriz Barreto-Duarte; Caio Sales; Mahomed-Yunus S Moosa; Matilda Mazibuko; Ginger L Milne; Fernanda Maruri; Carlos Henrique Serezani; John R Koethe; Marina C Figueiredo; Afrânio L Kritski; Marcelo Cordeiro-Santos; Valeria C Rolla; Timothy R Sterling; Alasdair Leslie; Bruno B Andrade
Journal:  Front Immunol       Date:  2022-07-08       Impact factor: 8.786
  1 in total

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