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Synthesis of arachidonic acid in the human placenta in …

T1 - Synthesis of arachidonic acid metabolites produced by purified kidney cortex microsomal cytochrome P-450

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The Synthesis of Arachidonic Acid Oxygenation …

(Matrix presented) Prostaglandin H synthase catalyzes the first committed step in the biosynthesis of prostaglandins and thromboxane. Herein we report the synthesis of four site-specifically labeled arachidonic acids for investigation of the radical intermediate formed during this enzymatic reaction. Two compounds were prepared using a common C9-C11 fragment, while another target was synthesized using a previously reported advanced intermediate. An alkyne coupling followed by hydrogenation and Wittig reaction was used to prepare the final labeled substrate.

T1 - Stimulation of arachidonic acid release and prostaglandin synthesis by bryostatin 1

N2 - Prostaglandin H synthase (PGHS) catalyzes the conversion of arachidonic acid to prostaglandin G2 in the cyclooxygenase reaction. The first step of the mechanism has been proposed to involve abstraction of the pro-S hydrogen atom from C13 to generate a pentadienyl radical spanning C11-C15. We report here the synthesis of six site-specifically deuterated arachidonic acids to investigate the structure of the radical intermediate. The preparation of these compounds was achieved using a divergent scheme that involved one advanced intermediate for all targets. The synthetic design introduced the label late in the routes and allowed the utilization of common synthetic intermediates in the preparation of various targets. Both 13(R)- and 13(S)-deuterium-labeled arachidonic acids were synthesized in high enantiomeric purity as deduced from soybean lipoxygenase assays and mass spectrometric analysis of the resulting enzymatic products. Each synthetic compound was reacted under anaerobic conditions with the wide singlet tyrosyl radical of PGHS-2 to generate a radical intermediate that was analyzed by EPR. Deuterium substitution at positions 11, 13(S), and 15 resulted in the loss of one hyperfine interaction, indicating that the protons at these positions interact with the unpaired electron. Simulation of the spectra was achieved with one set of parameters that are consistent with the assignment of a pentadienyl radical. Use of 16-[2H2]-arachidonic acid indicated that only one of the protons at C16 gives rise to a strong hyperfine interaction. The findings are discussed in the context of two proposed mechanisms for the cyclooxygenase reaction.

Synthesis of (19‐ 11 C)arachidonic acid - DeepDyve

T1 - Metabolism of arachidonic acid by canine polymorphonuclear leukocytes synthesis of lipoxygenase and omega-oxidized metabolites

AB - Reported are the synthesis and structure confirmation of the major metabolites produced during the NADPH dependent oxidation of arachidonic acid by a reconstituted enzyme system containing purified kidney cortex microsomal cytochrome P-450.

N2 - Reported are the synthesis and structure confirmation of the major metabolites produced during the NADPH dependent oxidation of arachidonic acid by a reconstituted enzyme system containing purified kidney cortex microsomal cytochrome P-450.

Arachidonic acid is not one of the essential fatty acids

T1 - Synthesis of isotopically labeled arachidonic acids to probe the reaction mechanism of prostaglandin H synthase

Prostaglandin H synthase (PGHS) catalyzes the conversion of arachidonic acid to prostaglandin G2 in the cyclooxygenase reaction. The first step of the mechanism has been proposed to involve abstraction of the pro-S hydrogen atom from C13 to generate a pentadienyl radical spanning C11-C15. We report here the synthesis of six site-specifically deuterated arachidonic acids to investigate the structure of the radical intermediate. The preparation of these compounds was achieved using a divergent scheme that involved one advanced intermediate for all targets. The synthetic design introduced the label late in the routes and allowed the utilization of common synthetic intermediates in the preparation of various targets. Both 13(R)- and 13(S)-deuterium-labeled arachidonic acids were synthesized in high enantiomeric purity as deduced from soybean lipoxygenase assays and mass spectrometric analysis of the resulting enzymatic products. Each synthetic compound was reacted under anaerobic conditions with the wide singlet tyrosyl radical of PGHS-2 to generate a radical intermediate that was analyzed by EPR. Deuterium substitution at positions 11, 13(S), and 15 resulted in the loss of one hyperfine interaction, indicating that the protons at these positions interact with the unpaired electron. Simulation of the spectra was achieved with one set of parameters that are consistent with the assignment of a pentadienyl radical. Use of 16-[2H2]-arachidonic acid indicated that only one of the protons at C16 gives rise to a strong hyperfine interaction. The findings are discussed in the context of two proposed mechanisms for the cyclooxygenase reaction.

AB - (Matrix presented) Prostaglandin H synthase catalyzes the first committed step in the biosynthesis of prostaglandins and thromboxane. Herein we report the synthesis of four site-specifically labeled arachidonic acids for investigation of the radical intermediate formed during this enzymatic reaction. Two compounds were prepared using a common C9-C11 fragment, while another target was synthesized using a previously reported advanced intermediate. An alkyne coupling followed by hydrogenation and Wittig reaction was used to prepare the final labeled substrate.

T1 - Synthesis of Site-Specifically Labeled Arachidonic Acids as Mechanistic Probes for Prostaglandin H Synthase
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  • 05/08/2011 · Synthesis of Arachid..

    T1 - Synthesis of Site-Specifically Labeled Arachidonic Acids as Mechanistic Probes for Prostaglandin H Synthase

  • The name prostaglandin derives ..

    Synthesis and metabolism of prostaglandins, prostacyclin, and thromboxanes: The arachidonic acid cascade

  • Arachidonic Acid - an overview | ScienceDirect Topics

    Biosynthesis of eicosanoids involves two steps: arachidonic acid release and its transformation into active products

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Glycemia, starch, and sugar in context - Ray Peat

N2 - (Matrix presented) Prostaglandin H synthase catalyzes the first committed step in the biosynthesis of prostaglandins and thromboxane. Herein we report the synthesis of four site-specifically labeled arachidonic acids for investigation of the radical intermediate formed during this enzymatic reaction. Two compounds were prepared using a common C9-C11 fragment, while another target was synthesized using a previously reported advanced intermediate. An alkyne coupling followed by hydrogenation and Wittig reaction was used to prepare the final labeled substrate.

What is Vitamin F: There Are Two Types of Vitamin F's

N2 - The mechanism of tumor promotion may involve stimulation of prostagladin production. Previous studies with the tumor promotor 12-O-tetradecanoylphorbol-13-acetate (TPA) have identified two effects of TPA on prostaglandin production. TPA stimulates both arachidonic acid release and de novo synthesis of prostaglandin H synthase. Activation of protein kinase C by TPA appears to be part of the mechanism to cause archidonic acid release. However, it is unclear if induction of prostaglandin H synthase also involves activation of protein kinase C. Bryostatin 1 is known to activate protein kinase C and to mimic some of the effects of TPA. We compared bryostatin 1 with TPA for the ability to cause arhidonic acid release and induced synthesis of prostaglandin H synthase. Bryostatin 1 induced arachidonic acid release and caused some prostaglandin production but only marginally induced synthesis of prostaglandin H synthase. Furthermore, we found that bryostatin 1 could inhibit the effect of TPA both in stimulation of arachidonic acid release and in the induction of prostaglandin H synthase.

What is Vitamin F, symptoms of stress, coping with stress:

The mechanism of tumor promotion may involve stimulation of prostagladin production. Previous studies with the tumor promotor 12-O-tetradecanoylphorbol-13-acetate (TPA) have identified two effects of TPA on prostaglandin production. TPA stimulates both arachidonic acid release and de novo synthesis of prostaglandin H synthase. Activation of protein kinase C by TPA appears to be part of the mechanism to cause archidonic acid release. However, it is unclear if induction of prostaglandin H synthase also involves activation of protein kinase C. Bryostatin 1 is known to activate protein kinase C and to mimic some of the effects of TPA. We compared bryostatin 1 with TPA for the ability to cause arhidonic acid release and induced synthesis of prostaglandin H synthase. Bryostatin 1 induced arachidonic acid release and caused some prostaglandin production but only marginally induced synthesis of prostaglandin H synthase. Furthermore, we found that bryostatin 1 could inhibit the effect of TPA both in stimulation of arachidonic acid release and in the induction of prostaglandin H synthase.

All mammalian cells except erythrocytes synthesize eicosanoids

(Matrix presented) Prostaglandin H synthase catalyzes the first committed step in the biosynthesis of prostaglandins and thromboxane. Herein we report the synthesis of four site-specifically labeled arachidonic acids for investigation of the radical intermediate formed during this enzymatic reaction. Two compounds were prepared using a common C9-C11 fragment, while another target was synthesized using a previously reported advanced intermediate. An alkyne coupling followed by hydrogenation and Wittig reaction was used to prepare the final labeled substrate.

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