Reactions of cysteine sulfenyl thiocyanate with thiols to give unsymmetrical disulfides

✍ Scribed by Susan L. Alguindigue Nimmo; Kelemu Lemma; Michael T. Ashby

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 96 KB
• Volume: 18
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20340

✦ Synopsis

Abstract

Cysteine sulfenyl thiocyanate (CSSCN) reacts with thiols at pH 0 to cleanly yield disulfides. 2‐Mercaptoethanol (2‐MESH), 3‐mercaptopropionic acid (3‐MPASH), penicillamine (PENSH), and glutathione (GSH) react with CSSCN to give the corresponding mixed disulfides: 2‐MESSC, 3‐MPASSC, PENSSC, and GSSC. These compounds are stable at pH 0 and have been characterized by ^1^H and ^13^C NMR spectroscopy. © 2007 Wiley Periodicals, Inc. 18:467–471, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20340