Preparation of Boc‐[S‐(3‐nitro‐2‐pyridinesulfenyl)]‐cysteine and its use for unsymmetrical disulfide bond formation
- 1 August 1986
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 28 (2), 107-112
- https://doi.org/10.1111/j.1399-3011.1986.tb03236.x
Abstract
The 3-nitro-2-pyridinesulfenyl (Npys) derivative of cysteine was prepared and used to facilitate the formation of an unsymmetrical disulfide bond. Since this derivative is stable in trifluoroacetic acid:CH2Cl2 (1:1) and anhydrous hydrogen fluoride, Boc-Cys(Npys) could be used directly in solid phase synthesis of the 14-peptide acetyl-Cys(Npys)-Gly-Glu-Gln-His-His-Pro-Gly-Gly-Gly-Ala-Lys-Gln-Ala-amide. Reaction of this peptide with the free thiol of another peptide, acetyl-Gly-Glu-Gln-His-His-Pro-Gly-Gly-Gly-Ala-Lys-Gln-Cys-amide, gave a single product containing an unsymmetrical disulfide bond. The amino acid composition of this product and HPLC analysis of its dithiothreitol reduction products were consistent with the desired heterodimer. As evidenced by HPLC, the mixed disulfide froms rapidly at alkaline pH and usefully over a wide pH range in aqueous buffers.Keywords
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