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.

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。