Preparation of trisulfide derivatives of cystine and their formation as by-products during peptide synthesis

The formation of a trisulfide derivative is observed when di-NH 2-protected cystine, is used during peptide synthesis. This side reaction occurs during the coupling step with several coupling reagents. A convenient method for the preparation of these derivatives in mild conditions is described. The...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 21; pp. 3531 - 3534
Main Authors Parmentier, B., Moutiez, M., Tartar, A., Sergheraert, C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.05.1994
Elsevier
Subjects
Analytical chemistry
Chemical Sciences
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Peptides
Physical Sciences
Preparations and properties
Science & Technology
Side reaction
Peptide synthesis
Organic trisulfide
Liquid phase
Sulfur peptide
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Summary:The formation of a trisulfide derivative is observed when di-NH 2-protected cystine, is used during peptide synthesis. This side reaction occurs during the coupling step with several coupling reagents. A convenient method for the preparation of these derivatives in mild conditions is described. The formation of stable trisulfide derivatives of cystine (n=3) has been detected during peptide synthesis. A method to prepare these compounds and higher polysulfides (n = 4 to 5) is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)73228-X