The Monoketo- and Monohydroxyoctadecanoic Acids. Preparation and Characterization by Thermal and X-ray Methods.

Bergström, Sune; Aulin-Erdtman, Gunhild; Rolander, B.; Stenhagen, Einar; Östling, Sven

doi:10.3891/acta.chem.scand.06-1157

Cited by 77 publications

(19 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The present work demonstrates that arachidonic acid is oxygenated in this system both by the cyclo-oxygenase involved in prostaglandin [5,6,8,9,11,12,14,Arachidonic acid was prepared as described (10). 12-Hydroxyeicosanoic acid was prepared by anodic coupling of 10-acetoxyoctadecanoic acid [80 mg, prepared by acetylation of lO-hydroxyoctadecanoic acid (11)1 and methyl hydrogen succinate (300 mg).…”

Section: Introductionmentioning

confidence: 89%

Prostaglandin Endoperoxides. Novel Transformations of Arachidonic Acid in Human Platelets

Hámberg

Samuelsson

1974

Proc. Natl. Acad. Sci. U.S.A.

1,207

359

View full text Add to dashboard Cite

Arachidonic acid incubated with human platelets was converted into three compounds, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, 12L-hydroxy-5,8,-10-beptadecatrienoic acid, and the hemiacetal derivative of 8-(1-hydroxy-3-oxopropyl)-9,12L-dihydroxy-5,10-heptadecadienoic acid. The formation of the two latter compounds from arachidonic acid proceeded by pathways involving the enzyme, fatty acid cyclo-oxygenase, in the initial step and with the prostaglandin endoperoxide, PGG2, as an intermediate. The first mentioned compound was formed from 12L-hydroperoxy-5,8,10,14-eicosatetraenoic acid, which in turn was formed from arachidonic acid by the action of a novel lipoxygenase. Aspirin and indomethacin inhibited the fatty acid cyclo-oxygenase but not the lipoxygenase, whereas 5,8,11,14-eicosatetraynoic acid inhibited both enzymes. The almost exclusive transformation of the endoperoxide structure into nonprostaglandin derivatives supports the hypothesis that the endoperoxides can participate directly and not by way of the classical prostaglandins in regulation of cell functions. The observed transformations of arachidonic acid in platelets also explain the aggregating effect of this acid.Prostaglandins (PG) E2 and F2a are formed and released by human platelets during aggregation induced by various agents (3,4). This biosynthetic capacity has also been demonstrated with labeled precursors (5, 6).Recent work in our laboratory led to the isolation (1) of an earlier postulated (7) endoperoxide intermediate in prostaglandin biosynthesis. This finding was confirmed and extended in subsequent studies in which an additional endoperoxide derivative, carrying a hydroperoxy group at C-15, was isolated (2,8). Studies of the aggregation of human platelets also demonstrated that the biosynthetic process can stop at the endoperoxide stage resulting in release of the intermediates (PGG2 and/or PGH2) (2). Since the endoperoxides were found to be potent aggregating agents and since blockade of their formation is accompanied by inhibition of the second wave of aggregation, it was suggested that they play a physiological role in this process (2).In connection with these and other studies it became of particular interest to further investigate the transformation of arachidonic acid by human platelets. The present work demonstrates that arachidonic acid is oxygenated in this system both by the cyclo-oxygenase involved in prostaglandin [5,6,8,9,11,12,14,Arachidonic acid was prepared as described (10). 12-Hydroxyeicosanoic acid was prepared by anodic coupling of 10-acetoxyoctadecanoic acid [80 mg, prepared by acetylation of lO-hydroxyoctadecanoic acid (11)1 and methyl hydrogen succinate (300 mg). The product was hydrolyzed and subjected to silicic acid chromatography and preparative thin-layer chromatography, giving 30 mg (39%) of pure 12-hydroxyeicosanoic acid. Thin-layer chromatography of the methyl ester showed a single spot with RF = 0.57. Gasliquid chromatographic analysis of the methyl ester showed a single peak with equivalent c...

show abstract

Section: Introductionmentioning

confidence: 89%

Prostaglandin Endoperoxides. Novel Transformations of Arachidonic Acid in Human Platelets

Hámberg

Samuelsson

1974

Proc. Natl. Acad. Sci. U.S.A.

1,207

359

View full text Add to dashboard Cite

show abstract

“…[7] . D-26h2:0 was racemized by Cr03-oxidation [8], purification of the 2-ketoester by silicic acid chromatography, reduction of the latter by NaBH, in methanol and purification of the DL-26h2 :0 by silicic acid chromatography.…”

Section: Introductionmentioning

confidence: 99%

Configuration of 2‐hydroxy acids from brain cerebrosides determined by gas chromatography

Hammarström

1969

FEBS Letters

View full text Add to dashboard Cite

“…The methyl (±)-αhydroxy stearate 5 is prepared in three steps from stearic acid 4 by bromination 12 using Hell-Volhard-Zelinsky conditions followed by hydrolysis 13 and esterification 14 in 88 % overall yield (Scheme 1). The methyl (±)-β-hydroxy stearate 8 was synthesized by the procedure described by Masamune 15 which involves homologation of palmitic acid 7 using in situ generated magnesium monomethylmalonate 16 to a preformed acyl imidazole to produce the β-keto stearic acid methyl ester, which is reduced 17 with sodium borohydride in ethanol providing 8 18 in 77 % overall yield (Scheme 2). The phosphoramidite approach was used for the synthesis of the lipid-nucleotide conjugates.…”

mentioning

confidence: 99%

Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents

Gangadhara

Lescrinier

Pannecouque

et al. 2014

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

Starting from thymidine, through a series of key synthetic transformations (e.g. Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 6' position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension. Graphical Abstract O OH HO N NH O O O N 3 N NH O O O P HO O O OH In coeval life, proteins and nucleic acids are intricately dependent upon each other for a host of functions. Protein enzymes (polymerases) are necessary for the synthesis of DNA and RNA, while nucleic acids (ribosomes) are necessary for the synthesis of proteins. According to the RNA world hypothesis, early life used nucleic acids for both information storage and chemical catalysis before the emergence of protein enzymes. However, it still remains unclear how nucleic acids were able to assemble and replicate before the advent of protein enzymes. This means that in contemporary life, proteins can catalyze phosphodiester bond formation (nucleic acid synthesis) and nucleic acids can catalyze amide bond formation (protein synthesis). Our motivation in this context comes from the recently proposed 'Molecular Midwife' hypothesis 1 and has the aim to investigate if

show abstract

The Monoketo- and Monohydroxyoctadecanoic Acids. Preparation and Characterization by Thermal and X-ray Methods.

Cited by 77 publications

References 0 publications

Prostaglandin Endoperoxides. Novel Transformations of Arachidonic Acid in Human Platelets

Prostaglandin Endoperoxides. Novel Transformations of Arachidonic Acid in Human Platelets

Configuration of 2‐hydroxy acids from brain cerebrosides determined by gas chromatography

Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents

Contact Info

Product

Resources

About