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过敏反应迟缓反应物质,SRS - A;立体化学的确定

Slow reacting substance of anaphylaxis, SRS-A; assignment of the stereochemistry.

作者信息

Morris H R, Taylor G W, Rokach J, Girard Y, Piper P J, Tippins J R, Samhoun M N

出版信息

Prostaglandins. 1980 Sep;20(3):601-7. doi: 10.1016/0090-6980(80)90047-7.

DOI:10.1016/0090-6980(80)90047-7
PMID:7422903
Abstract

We have recently described the structure elucidation of slow reacting substance of anaphylaxis S(SRS-A) from lung and of a slow reacting substance (SRS) from basophilic leukaemia cells as 5-hydroxy-6-cysteinylglycinyl-7,9,11,14-eicosatetraenoic acid. The stereochemistry of this molecule has now been shown to be 5(S)-hydroxy- 6(R)-cysteinylghlycinyl-7,9-trans-11,14-ciseicosatetraenoic acid by comparison of the synthetic and natural products and their derivatives using mass spectrometric and HPLC chromatographic techniques. The synthetic and natural compounds are also indistinguishable by their pharmacological properties, their conversion by soybean lipoxygenase, and their UV spectra.

摘要

我们最近已将从肺中提取的过敏反应慢反应物质S(SRS-A)以及从嗜碱性白血病细胞中提取的慢反应物质(SRS)的结构解析为5-羟基-6-半胱氨酰甘氨酰-7,9,11,14-二十碳四烯酸。通过使用质谱和高效液相色谱技术比较合成产物与天然产物及其衍生物,现已证明该分子的立体化学结构为5(S)-羟基-6(R)-半胱氨酰甘氨酰-7,9-反式-11,14-顺式二十碳四烯酸。合成化合物与天然化合物在药理特性、经大豆脂氧合酶的转化以及紫外光谱方面也无法区分。

相似文献

1
Slow reacting substance of anaphylaxis, SRS-A; assignment of the stereochemistry.过敏反应迟缓反应物质,SRS - A;立体化学的确定
Prostaglandins. 1980 Sep;20(3):601-7. doi: 10.1016/0090-6980(80)90047-7.
2
A comparative study of the physical properties and enzymatic reactions of slow reacting substance of anaphylaxis and some leukotriene D4 isomers.过敏反应迟缓反应物质与一些白三烯D4异构体的物理性质及酶促反应的比较研究
Prostaglandins. 1982 Apr;23(4):569-77. doi: 10.1016/0090-6980(82)90117-4.
3
Slow-reacting substances and their structural elucidation.慢反应物质及其结构解析
Ciba Found Symp. 1980;78:203-15. doi: 10.1002/9780470720615.ch11.
4
Structure of slow-reacting substance of anaphylaxis (SRS-A).过敏反应慢反应物质(SRS-A)的结构。
Prostaglandins. 1980 Oct;20(4):655-66. doi: 10.1016/0090-6980(80)90106-9.
5
Slow-reacting substances and their formation by a lipoxygenase pathway.慢反应物质及其通过脂氧合酶途径的形成。
Agents Actions. 1980 Dec;10(6):541-7. doi: 10.1007/BF02024161.
6
Slow reacting substances (SRSs): the structure identification of SRSs from rat basophil leukaemia (RBL-1) cells.慢反应物质(SRSs):大鼠嗜碱性粒细胞白血病(RBL-1)细胞中慢反应物质的结构鉴定
Prostaglandins. 1980 Feb;19(2):185-201. doi: 10.1016/0090-6980(80)90019-2.
7
Slow reacting substances of anaphylaxis: identification of leukotrienes C-1 and D from human and rat sources.过敏反应迟缓反应物质:从人和大鼠来源中鉴定白三烯C-1和D
Proc Natl Acad Sci U S A. 1980 Jun;77(6):3710-4. doi: 10.1073/pnas.77.6.3710.
8
Comparison of rat, mouse, guinea-pig and human slow reacting substance of anaphylaxis (SRS-A).大鼠、小鼠、豚鼠和人类过敏反应迟缓反应物质(SRS-A)的比较。
Experientia. 1979 Mar 15;35(3):361-3. doi: 10.1007/BF01964353.
9
Comparative studies on immunologically and non-immunologically produced slow-reacting substances from man, guinea-pig and rat.关于人、豚鼠和大鼠免疫性和非免疫性产生的慢反应物质的比较研究。
Br J Pharmacol. 1979 Oct;67(2):179-84. doi: 10.1111/j.1476-5381.1979.tb08664.x.
10
On the preparation of highly purified slow reacting substance of anaphylaxis (SRS-A) from biological extracts.关于从生物提取物中制备高纯度过敏反应迟缓反应物质(SRS-A)
Br J Pharmacol. 1980 Jan;68(1):33-46. doi: 10.1111/j.1476-5381.1980.tb10696.x.

引用本文的文献

1
Lipoxygenase inhibitory activity of U-66,858 and its deacetylated metabolite U-68,244 in human whole blood.U-66,858及其脱乙酰代谢物U-68,244在人全血中的脂氧合酶抑制活性。
Agents Actions. 1994 Mar;41(1-2):32-6. doi: 10.1007/BF01986390.
2
[Increase of pulmonary vascular resistance and permeability due to the metabolism of free arachidonic acid (author's transl)].游离花生四烯酸代谢导致肺血管阻力和通透性增加(作者译)
Klin Wochenschr. 1981 May 4;59(9):459-61. doi: 10.1007/BF01695900.
3
Stimulation of arachidonic acid metabolism and generation of thromboxane A2 by leukotrienes B4, C4 and D4 in guinea-pig lung in vitro.
白三烯B4、C4和D4对豚鼠肺组织花生四烯酸代谢的刺激作用及体外血栓素A2的生成
Br J Pharmacol. 1982 Oct;77(2):267-75. doi: 10.1111/j.1476-5381.1982.tb09295.x.
4
Slow reacting substances (leukotrienes): enzymes involved in their biosynthesis.慢反应物质(白三烯):参与其生物合成的酶。
Proc Natl Acad Sci U S A. 1982 Aug;79(16):4838-42. doi: 10.1073/pnas.79.16.4838.
5
Zymosan enhances leukotriene D4 metabolism by porcine alveolar macrophages.酵母聚糖可增强猪肺泡巨噬细胞对白三烯D4的代谢。
Immunology. 1985 Sep;56(1):153-9.