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Protein & Peptide Letters

Editor-in-Chief

ISSN (Print): 0929-8665
ISSN (Online): 1875-5305

Research Article

N-Chlorosuccinimide-Mediated Oxidative Chlorination of Thiols to Nα -Protected Amino Alkyl Sulfonyl Azides and Their Utility in the Synthesis of Sulfonyl Triazole Acids

Author(s): Sharnabai. K. M, Krishnamurthy. M, Sagar. N. R, Santhosh. L and Vommina V. Sureshbabu

Volume 24, Issue 1, 2017

Page: [56 - 63] Pages: 8

DOI: 10.2174/0929866523666161130151218

Price: $65

Abstract

An efficient oxidative chlorination of thiols to Nα-protected amino alkyl sulfonyl azides is delineated. The reaction involves in situ generation of sulfonyl chloride employing Nchlorosuccinimide and tetrabutylammonium chloride-water in acetonitrile, followed by the reaction with sodium azide. The protocol is simple, straight forward, mild and high yielding. Amino acids with simple as well as bifunctional side chains were used to obtain Nα-protected amino alkyl sulfonyl azides. Further, sulfonyl azides were utilized to synthesize unnatural amino acids via Cu(OAc)2.H2O/2-amino phenol catalyzed Click reaction with propiolic acid.

Keywords: Nα-protected thiols, Nα-protected amino alkyl sulfonyl azides, sulfonyl triazole acid, Click reaction.

Graphical Abstract

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