3-NITRO-2-PYRIDINESULFENYL GROUP FOR PROTECTION AND ACTIVATION OF THE THIOL FUNCTION OF CYSTEINE
3-NITRO-2-PYRIDINESULFENYL GROUP FOR PROTECTION AND ACTIVATION OF THE THIOL FUNCTION OF CYSTEINE
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用于保护和激活半胱氨酸硫醇功能的 3-硝基-2-吡啶亚磺基
DOI：
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发表时间：
1981
期刊：
影响因子：
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通讯作者：
G. Matsueda
中科院分区：
文献类型：
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作者：
R. Matsueda;Takahide Kimura;E. Kaiser;G. Matsueda
使用3-硝基-2-吡啶硫基（Npys）卤化物，在肽化学中的通用试剂，用于保护和活化的硫醇功能的报告。从双（N-叔丁氧基羰基）-L-胱氨酸开始制备Boc-Cys（Npys）-OH。Npys基团很容易通过在水的存在下用化学计量的三正丁基膦处理而除去，但它对酸如三氟乙酸、HCl和HF具有抗性。重要的是，用Npys基团修饰的半胱氨酸残基可以选择性地与半胱氨酸的游离巯基反应以提供胱氨酸二硫键。
The use of the 3-nitro-2-pyridinesulfenyl (Npys) halide, a versatile reagent in peptide chemistry, for the protection and activation of the thiol function is reported. Boc-Cys(Npys)–OH is prepared starting from bis(N-t-butyloxycarbonyl)-L-cystine. The Npys group is easily removed by treatment with a stoichiometric amount of tri-n-butylphosphine in the presence of water, but it is resistant to acids such as trifluoroacetic acid, HCl, and HF. Importantly, the cysteine residue modified with the Npys group can react selectively with free thiol of cysteine to afford a cystine disulfide bond.