Disulfide linkage to polyacrylic resin for automated Fmoc peptide synthesis. Immunochemical applications of peptide resins and mercaptoamide peptides.
The use of disulfide bonds for peptide-resin linkage in solid-phase peptide synthesis was investigated using polyacrylic polymers (Expansin) and automated Fmoc methodology. The disulfide moiety was bound to the support either by coupling a protected bifunctional handle or by an original stepwise procedure. Among the three different disulfide handles that were investigated, only the aminoethyldithio-2-isobutyric acid (AEDI) handle was stable enough to achieve peptide synthesis. A series of peptides of up to 10-20 amino acids were prepared in this manner, in good yield and purity. Rapid and quantitative peptide release was obtained by reduction with equimolecular amounts of dithiothreitol at pH 9 or tris(2-carboxymethyl) phosphine at pH 4.5. This allowed direct and rapid coupling of the released cysteamide peptides to an activated protein carrier and the use of free or resin-bound forms of the antigen in immunoassays.
Méry
J
J
Research Centre for Macromolecular Biochemistry, CNRS, Montpellier, France.
Granier
C
C
Juin
M
M
Brugidou
J
J
D000180:Acrylic Resins; D000595:Amino Acid Sequence; D004220:Disulfides / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry; D007120:Immunochemistry; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry / Q000276:immunology; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology
D000180:Acrylic Resins; D004220:Disulfides; D005449:Fluorenes; D009842:Oligopeptides; D010455:Peptides