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Literature DB >> 16951707

Convenient syntheses of [20,20,20-H(3)]-arachidonic acid and [20,20-H(2)]-20-hydroxyeicosatetraenoic acid.

J R Falck, Siddam Anjaiah, Venugopal Raju Tuniki, V Raj Gopal, Jorge H Capdevila.

Abstract

Deuterated arachidonic acid and 20-HETE were prepared in good overall yields and high stereoselectivities. Key transformations include a trans-specific vinyl dibromide reduction and Suzuki cross-couplings to a lithium borate or a 9-BBN borane. These standards are three and two mass units higher, respectively, than their naturally occurring counterparts and are useful in mass spectrometry analysis.

Entities: Chemical

Year: 2006 PMID： 16951707 PMCID： PMC1414091 DOI： 10.1002/jlcr.1039

Source DB: PubMed Journal: J Labelled Comp Radiopharm ISSN： 0362-4803 Impact factor: 1.921

21 in total

Review 1. Biochemical and molecular properties of the cytochrome P450 arachidonic acid monooxygenases.

Authors: Jorge H Capdevila; John R Falck
Journal: Prostaglandins Other Lipid Mediat Date: 2002-08 Impact factor: 3.072

2. Measurement of 20-hydroxyeicosatetraenoic acid in human urine by gas chromatography-mass spectrometry.

Authors: Jennifer Rivera; Natalie Ward; Jonathan Hodgson; Ian B Puddey; John R Falck; Kevin D Croft
Journal: Clin Chem Date: 2004-01 Impact factor: 8.327

3. 20-Hydroxyeicosatetraenoic acid is excreted as a glucuronide conjugate in human urine.

Authors: C Prakash; J Y Zhang; J R Falck; K Chauhan; I A Blair
Journal: Biochem Biophys Res Commun Date: 1992-06-15 Impact factor: 3.575

4. Production of 20-HETE and its role in autoregulation of cerebral blood flow.

Authors: D Gebremedhin; A R Lange; T F Lowry; M R Taheri; E K Birks; A G Hudetz; J Narayanan; J R Falck; H Okamoto; R J Roman; K Nithipatikom; W B Campbell; D R Harder
Journal: Circ Res Date: 2000-07-07 Impact factor: 17.367

Review 5. 20-HETE and the kidney: resolution of old problems and new beginnings.

Authors: J C McGiff; J Quilley
Journal: Am J Physiol Date: 1999-09

6. Quantitation of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) produced by human polymorphonuclear leukocytes using electron capture ionization gas chromatography/mass spectrometry.

Authors: E Hill; R C Murphy
Journal: Biol Mass Spectrom Date: 1992-05

7. High-performance liquid chromatograpy-thermospray mass spectrometry of omega-hydroxy polyunsaturated fatty acids from rat brain homogenate.

Authors: M Yamane; A Abe; M Nakajima
Journal: J Chromatogr B Biomed Appl Date: 1994-12-02

8. Separation of unlabeled metabolites of arachidonic acid from their deuterium- and tritium-labeled analogs by argentation high-pressure liquid chromatography.

Authors: W S Powell
Journal: Anal Biochem Date: 1983-01 Impact factor: 3.365