Synthesis of side chain-protected amino acid phenylthiohydantoins and their use in quantitative solid-phase Edman degradation.
Solid-phase Edman degradation of synthetic peptidyl-resins has been used advantageously to detect errors of deletion which might occur during Merrifield peptide synthesis. To facilitate complete quantitation of the resulting phenylthiohydantoin(PTH)-amino acids, the PTH derivatives of the following side chain-protected amino acid residues have been synthesized: Arg(Tos), Asp(OBzl), Cys(3,4-(CH3)2-Bzl), Glu(OBzl), Lys(2-ClZ), Ser(Bzl), Thr(Bzl), Tyr(2-BrZ), and Tyr(2,6-Cl2Bzl). For each derivative, a melting point, elemental analysis, and extinction coefficient were obtained. With these new compounds as HPLC standards, an unequivocal assignment and quantification of each side chain protected amino acid was possible. A quantitative analysis was performed for six model peptides with the general formula Ala-X-Leu-Y-Ala-Gly-NHCH2-resin (where X and Y represented different side chain-protected amino acyl residues). We have found solid-phase Edman degradation to be a useful aid for the characterization of peptides when they are used unpurified as synthetic antigens.
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis*; D002021:Buffers; D055598:Chemical Phenomena; D002621:Chemistry; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D004126:Dimethylformamide; D006827:Hydantoins / Q000138:chemical synthesis*; D010455:Peptides / Q000032:analysis* / Q000138:chemical synthesis; D010669:Phenylthiohydantoin / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D011437:Propylamines
D000596:Amino Acids; D002021:Buffers; D006827:Hydantoins; D010455:Peptides; D011437:Propylamines; D010669:Phenylthiohydantoin; D004126:Dimethylformamide; C007442:diisopropylamine