104523-33-3Relevant academic research and scientific papers
Disulfide bond formation using the silyl chloride-sulfoxide system for the synthesis of a cystine peptide
Akaji, Kenichi,Tatsumi, Tadashi,Yoshida, Makoto,Kimura, Tooru,Fujiwara, Yoichi,Kiso, Voshiaki
, p. 4137 - 4143 (2007/10/02)
An efficient method for disulfide bond formation in peptides by the silyl chloride-sulfoxide system is described. Methyltrichlorosilane in trifluoroacetic acid, in the presence of diphenyl sulfoxide, is found to cleave various S-protecting groups of cysteine to form cystine directly within 10-30 min. No side reactions were observed with nucleophilic amino acids such as Met, His, or Tyr, except for Trp, under the reaction conditions of the silyl chloride-sulfoxide treatment. A chlorination of the indole moiety of unprotected Trp, rather than sulfur-sulfur bond formation, is a dominant reaction when the peptide containing unprotected Trp is treated with the chlorosilane-sulfoxide. However, the disulfide bond can be formed efficiently with no modification at the indole ring by treatment of the peptide having a formyl-protected Trp residue with the silyl chloride-sulfoxide system. The formyl group is removed by a brief treatment at basic pH without affecting the disulfide bond formed by the silyl chloride-sulfoxide treatment. This new disulfide bond forming reaction in trifluoroacetic acid is successfully applied to the syntheses of oxytocin, human brain natriuretic peptide, and somatostatin without any solubility problem.
Peptide Synthesis. Part 6. Protection of the Sulphydryl Group of Cysteine in Solid-phase Synthesis using Nα-Fluorenylmethoxycarbonylamino Acids. Linear Oxytocin Derivatives
Atherton, Eric,Pinori, Masimo,Sheppard, Robert C.
, p. 2057 - 2064 (2007/10/02)
The Nα-fluorenylmethoxycarbonyl derivatives of S-acetamidomethyl-, S-t-butyl-, and S-S-t-butyl-cysteine have been prepared and used in solid-phase peptide synthesis on polar, poly(dimethylacrylamide) supports.All three derivatives proved suitable as judged by synthesis of the linear oxytocin nonapeptide amide sequence.
