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Selective Removal of the o-Nitrophenylsulfenyl Protecting Group in Peptide Synthesis

✍ Scribed by Aung Tun-Kyi

Publisher
John Wiley and Sons
Year
1978
Tongue
German
Weight
304 KB
Volume
61
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

2‐Thiopyridone (2‐mercaptopyridine, 1) was found to be a very suitable reagent for removing the N^α^‐o‐nitrophenylsulfenyl (NPS‐) group in both conventional and solid‐support peptide synthesis. A 3‐ to 5‐molar excess of the reagent together with an equivalent amount of glacial acetic acid in methanol, dimethylformamide, or methylene chloride produces the soluble, stable mixed disulfide, 2‐nitrophenyl 2‐pyridyl disulfide (2), and the N^α^‐deprotected amino‐acid or peptide. The yields are quantitative in less than 5 min if all educts are dissolved, in about 20 to 30 min in solid‐support synthesis. No modifications of either the indole side‐chain of tryptophan or of a series of side‐chain protecting groups, in particular of the t‐butyl type, are produced. No adverse side‐reactions (insoluble disulfides) were observed. The procedure is illustrated with a series of amino‐acid derivatives and with the solid‐support synthesis of [5‐leucine]‐enkephalin.

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