Controlled peptide‐protein conjugation by means of 3‐nitro‐2‐pyridinesulfenyl protection‐activation
- 1 September 1988
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 32 (3), 161-166
- https://doi.org/10.1111/j.1399-3011.1988.tb00930.x
Abstract
The disulfide bond in S-3-nitro-2-pyridinesulfenyl (S-Npys) compounds is stable towards the acid treatment used in solid-phase peptide synthesis, yet the lability of S-Npys-peptides towards nucleophiles enables the conjugation to proteins to proceed under mild conditions. Thus Boc-Cys(Npys)-OH was coupled as N-terminal residue to a resin-linked peptide chain. After deprotection and cleavage from the resin the Npys-cysteinylpeptide was attached to a properly functionalized protein by reaction with a mercapto group. The amount of peptide conjugated to the protein was determined by measuring the amount of 3-nitro-2-thiopyridone liberated. The cysteinylpeptide which was detached from the protein by reduction of the disulfide bond was shown to be identical with the product obtained by reduction of the Npys-cysteinylpeptide.Keywords
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