PMID: 3771096Aug 1, 1986Paper

Preparation of Boc-[S-(3-nitro-2-pyridinesulfenyl)]-cysteine and its use for unsymmetrical disulfide bond formation

International Journal of Peptide and Protein Research
M S BernatowiczG R Matsueda

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:CH2 Cl2 (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-Gln-His-His-Pro-Gly-Gly-Gly-Ala-Lys-G ln-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 forms rapidly at alkaline pH and usefully over a wide pH range in aqueous buffers.

References

Nov 23, 1971·Biochemistry·R Chen, R F Doolittle
Jan 1, 1967·The Journal of Organic Chemistry·R G HiskeyE L Smithwick
Sep 1, 1983·International Journal of Peptide and Protein Research·J D YoungG R Matsueda
May 1, 1982·International Journal of Peptide and Protein Research·R J RidgeR Matsueda

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Citations

Nov 22, 2016·Chembiochem : a European Journal of Chemical Biology·Saskia A BodeDennis W P M Löwik
Sep 1, 1988·International Journal of Peptide and Protein Research·J W DrijfhoutW Bloemhoff
Aug 1, 1993·International Journal of Peptide and Protein Research·K C PughJ M Stewart
Mar 29, 2014·Chemistry : a European Journal·Melanie RauschenbergBart Jan Ravoo
Apr 14, 2017·Chemistry : a European Journal·Akihiro TaguchiYoshio Hayashi
Oct 15, 1996·European Journal of Biochemistry·E E Büllesbach, C Schwabe
May 27, 2017·Angewandte Chemie·Luis Moroder, Hans-Jürgen Musiol
Jan 26, 2017·Journal of Peptide Science : an Official Publication of the European Peptide Society·Cédric RentierYoshio Hayashi
Feb 11, 2020·Chemical Communications : Chem Comm·Yuteng WuChristian Heinis
Dec 1, 1987·International Journal of Peptide and Protein Research·G BaranyD G Mullen
Apr 15, 2009·Chemical Reviews·Albert Isidro-LlobetFernando Albericio
Mar 20, 2014·Bioconjugate Chemistry·Oleg MelnykPatricia Melnyk
Dec 4, 2019·The Journal of Organic Chemistry·Akihiro TaguchiYoshio Hayashi
Jun 5, 2004·The Journal of Organic Chemistry·Julio A CamareroAlexander R Mitchell

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