Reactive sulfur species: Aqueous chemistry of sulfenyl thiocyanates
Reactive sulfur species: Aqueous chemistry of sulfenyl thiocyanates
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DOI：
10.1021/ja048585a
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发表时间：
2004-08-25
影响因子：
15
通讯作者：
Aneetha, H
中科院分区：
文献类型：
--
作者：
Ashby, MT;Aneetha, H
在pH = 0的条件下原位合成了青霉胺（PENSCN）和谷胱甘肽（GSSCN）的硫氰基硫氰酸酯（RSSCN）衍生物，该衍生物由次硫氰酸（HOSCN）、硫氰原（(SCN)2）和三硫氰酸酯（(SCN)3-）组成。亲电硫氰化剂n -硫氰化丁二酰亚胺（NTS）也与PEN和GSH反应生成相应的RSSCN衍生物。采用NMR、ES-MS和IR对PENSCN和GSSCN进行了表征。虽然在pH = 0时稳定，但在较高的pH下，RSSCN衍生物分解产生的产物与水解和反应性亚磺酸的形成一致。
Sulfenyl thiocyanate (RSSCN) derivatives of penicillamine (PENSCN) and glutathione (GSSCN) have been synthesized in situ at pH = 0 from equilibrium mixtures that consists of hypothiocyanous acid (HOSCN), thiocyanogen ((SCN)2), and trithiocyanate ((SCN)3-). The electrophilic thiocyanating agentN-thiocyanatosuccinimide (NTS) also reacts with PEN and GSH to yield the corresponding RSSCN derivatives. PENSCN and GSSCN were characterized by NMR, ES-MS, and IR spectroscopy. While stable at pH = 0, at higher pH the RSSCN derivatives decompose to give products that are consistent with hydrolysis and formation of reactive sulfenic acids.