Disulfide bond-forming reaction using a dimethyl sulfoxide/aqueous HCl system and its application to regioselective two disulfide bond formation.
Disulfide bond-forming reaction using a dimethyl sulfoxide/aqueous HCl system and its application to regioselective two disulfide bond formation.
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使用二甲亚砜/HCl 水溶液体系的二硫键形成反应及其在区域选择性两个二硫键形成中的应用。
DOI：
10.1111/j.1399-3011.1995.tb01043.x
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
N. Fujii
中科院分区：
文献类型：
--
作者：
H. Tamamura;A. Otaka;J. Nakamura;K. Okubo;T. Koide;K. Ikeda;T. Ibuka;N. Fujii
描述了通过用三氟甲磺酸银（AgOTf）和二甲亚砜（DMSO）/HCl水溶液连续处理在含S-乙酰氨基甲基（Acm）半胱氨酸的肽中形成二硫键。发现S-Acm半胱氨酸通过用AgOTf脱保护Acm基团，然后用DMSO/HCl水溶液处理而定量转化为半胱氨酸。在这些反应条件下，没有观察到氧化敏感性氨基酸如Met、Tyr和Trp的显著副反应。催产素和含色氨酸的肽，尾加压素II，通过这种方法制备。此外，区域选择性的两个二硫键的形成被认为是可行的空气氧化和AgOTf-DMSO/HCl系统的组合。该策略已成功地应用于分子中含有两个二硫键和一个Trp残基的鲎素I和内皮素I的合成。
Disulfide bond formation in S-acetamidomethyl (Acm) cysteine-containing peptides by successive treatments with silver trifluoromethanesulfonate (AgOTf) and dimethyl sulfoxide (DMSO)/aqueous HCl is described. An S-Acm cysteine was found to be quantitatively converted into cysteine by deprotection of the Acm group with AgOTf followed by DMSO/aqueous HCl treatment. Under these reaction conditions, no significant side reactions were observed with oxidation-sensitive amino acids such as Met, Tyr and Trp. Oxytocin and a Trp-containing peptide, urotensin II, were prepared by this method. Furthermore, regioselective two disulfide bond formation was found to be feasible by the combination of air oxidation and the AgOTf-DMSO/HCl system. This strategy has been successfully applied to the syntheses of tachyplesin I and endothelin I, which have two disulfide bonds and a Trp residue in the molecule.