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
This publication has 14 references indexed in Scilit:
- Sulfur protection with the 3‐nitro‐2‐pyridinesulfenyl group in solid‐phase peptide synthesisInternational Journal of Peptide and Protein Research, 1982
- 3-NITRO-2-PYRIDINESULFENYL GROUP FOR PROTECTION AND ACTIVATION OF THE THIOL FUNCTION OF CYSTEINEChemistry Letters, 1981
- A STABLE PYRIDINESULFENYL HALIDEChemistry Letters, 1978
- Sulfur-Containing Polypeptides XVII. The S-Carbomethoxysulfenyl Derivatives as a Protective Group for CysteineThe Journal of Organic Chemistry, 1975
- Die gezielte Synthese offenkettiger asymmetrischer Cystinpeptide mittels thiol‐induzierter Fragmentierung von Sulfenylthiocarbonanten. Insulinfragmente mit intakter Disulfidbrücke A20‐B19.Helvetica Chimica Acta, 1973
- γ-γ Cross-linking sites in human and bovine fibrinBiochemistry, 1971
- New synthetic concepts in organosulfur chemistry. I. New pathway to unsymmetrical disulfides. The thiol-induced fragmentation of sulfenyl thiocarbonatesJournal of the American Chemical Society, 1970
- Sulfur-containing polypeptides. XII. Scope and limitations of the sulfenylthiocyanate method as a route to cystine peptidesThe Journal of Organic Chemistry, 1970
- Chemistry of Aliphatic Disulfides. V. Preparation of Some Open-chain Unsymmetrical Cystine Derivatives from Thioethers of CysteineJournal of the American Chemical Society, 1962