Disulfide bond as peptide-resin linkage in Boc-Bzl SPPS, for potential biochemical applications.
Use of disulfide bonds for labile linkage in solid-phase peptide synthesis was investigated using polyacrylic polymers (Expansin). Three bifunctional disulfide handles were synthesized for the introduction of disulfide linkage to the synthesis support. This work showed that only N-Boc aminoethyl 2-propionic acid and N-Boc aminoethyl 2-isobutyric acid were fully compatible with Boc/Bzl peptide synthesis and trifluoromethane sulfonic acid side-chain protection. Qualitative and quantitative synthesis results were comparable to those obtained by conventional peptide synthesis using polyacrylic resins. The resulting peptidyl-resins, which swelled in water or aqueous buffers, may be suitable for various biochemical applications, including use as peptide-resin conjugates for antibody production. Thiolysis by aqueous dithiothreitol released mercapto amide peptides suitable for various uses in solution (e.g., direct coupling with activated protein carrier, specific labeling in the mercapto amide group). Partial thiolysis of the disulfide linkage allowed easy post-synthetic adjustment of the peptide loading of peptidyl-resins.
Mery
J
J
Centre de Recherche de Biochimie Macromoléculaire, UPR 9008 C.N.R.S., Montpellier, France.
Brugidou
J
J
Derancourt
J
J
D000595:Amino Acid Sequence; D000818:Animals; D016203:CDC2 Protein Kinase / Q000138:chemical synthesis / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry*; D007987:Gonadotropin-Releasing Hormone / Q000031:analogs & derivatives / Q000138:chemical synthesis; D008698:Mesylates; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000138:chemical synthesis / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives; D012116:Resins, Plant / Q000737:chemistry*; D013438:Sulfhydryl Compounds; D014982:Xenopus laevis
D004220:Disulfides; D008698:Mesylates; D010446:Peptide Fragments; D010455:Peptides; D012116:Resins, Plant; D013438:Sulfhydryl Compounds; C062418:PSTAIR peptide; C078002:CDC2 peptide (9-19); C078000:LHRH cysteamide, des-Arg-; D007987:Gonadotropin-Releasing Hormone; D016203:CDC2 Protein Kinase; C012077:trifluoromethanesulfonic acid; D011761:Pyrrolidonecarboxylic Acid