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Prostaglandin A3

(Synonyms: 胃蛋白酶A) 目录号 : GC40765

Exhibits good affinity for canine EP2 and EP4 receptors

Prostaglandin A3 Chemical Structure

Cas No.:36614-31-0

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25μg
¥1,352.00
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50μg
¥2,228.00
现货
100μg
¥4,112.00
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Sample solution is provided at 25 µL, 10mM.

产品文档

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产品描述

Cyclooxygenase metabolism of EPA to produce Prostaglandin E3 (PGE3) has been reported in biosynthetic preparations of ovine seminal vesicles and in the ocular tissues of primates. Prostaglandin A3 (PGA3) is an expected non-enzymatic dehydration product of this PGE3. PGA3 exhibits good affinity for the canine EP2 and EP4 receptors with IC50 values of 120 nM and 20 nM, respectively, in a radioligand binding assay. PGA3 has weak affinity for human PPARγ, with a Ki value of 188 µM.

Chemical Properties

Cas No. 36614-31-0 SDF
别名 胃蛋白酶A
Canonical SMILES O=C1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)C/C=C\CC)C=C1
分子式 C20H28O4 分子量 332.4
溶解度 DMF: >75 mg/ml (from PGA1),DMSO: >50 mg/ml (from PGA1),Ethanol: >100 mg/ml (from PGA1),PBS pH 7.2: >2.4 mg/ml (from PGA1) 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 3.0084 mL 15.0421 mL 30.0842 mL
5 mM 0.6017 mL 3.0084 mL 6.0168 mL
10 mM 0.3008 mL 1.5042 mL 3.0084 mL
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Research Update

Formation of prostaglandin A analogues via an allene oxide

J Biol Chem 1990 Apr 25;265(12):6705-12.PMID:2324098doi

One potential biosynthetic route to the prostaglandins involves the participation of lipoxygenase and allene oxide synthase enzymes, giving a hydroxylated allene oxide, which then might cyclize to form prostaglandin A or a close analogue. We have tested a model of this type of transformation using 8-hydroxy-15S-hydroperoxy eicosanoids as substrates for the dehydrase (allene oxide synthase) in flaxseed. Four of these substrates, each with a 9E,11Z,13E-conjugated triene, gave an observable rate of reaction. The two derived from eicosapentaenoic acid reacted more rapidly than the corresponding arachidonic acid analogues. Also, the 8S-hydroxy-15S-hydroperoxy diastereomers reacted more rapidly than their 8R-hydroxy analogues. Products were characterized by high pressure liquid chromatography, UV, gas chromatography-mass specrometry, 1H NMR, and CD. Reaction of the (8S)-hydroxy-(15S)-hydroperoxy-eicosapentaenoic acid gave two alpha-ketols [8S),15-dihydroxy-14-oxoeicosa-5Z,9E,11Z,17Z+ ++-tetraenoic acid and the corresponding 11E isomer in a 2:1 ratio), together with four Prostaglandin A3 analogues which differed in the configurations of the side chains. Oxygen 18 labeling fully supported the intermediacy of an allene oxide in the biosynthesis. The corresponding "8R" substrate was converted to the enantiomers of these products plus three 13-hydroxy-14,15-epoxy derivatives. The arachidonate analogues formed the epoxy-hydroxy derivatives, the alpha-ketols, and two prostaglandin A2 analogues with trans configuration of the side chains. These results demonstrate (i) a feasible route of metabolism of lipoxygenase products to hydroxy allene oxide, (ii) the potential for the resulting allene oxide to cyclize to a prostaglandin A analogue, and (iii) the marked influence of the hydroxyl configuration of the rate of reaction and resulting profile of products. Some of these reactions may occur in a natural pathway of prostanoid biosynthesis in corals and other organisms.