title: A gentle method for linking Tris to amino acids and peptides.
abstract: A gentle method for the addition of Tris to the carboxyl group of amino acids or peptides for the purpose of altering their solubility and/or for providing sites for further derivatization is described. Under mild alkaline conditions and in high concentrations of aqueous dimethylformamide, the amino group of Tris cleaves simple esters of N-protected amino acids or peptides to form an amino acid-Tris linkage. The effects of pH, temperature and dimethylformamide concentration on the rate and the efficiency of the reaction of Tris with benzyloxycarbonyl-alanine methyl ester were examined and the general applicability of the method demonstrated on a range of amino acid and small peptide substrates. Side-chain protection was not required and the degree of racemization was found to be lower than with conventional chemical coupling.
authors.affiliation: CSIRO Division of Biomolecular Engineering, Sydney Laboratory, NSW, Australia.
authors.forename: R G
authors.initials: RG
authors.lastname: Whittaker
authors.forename: P J
authors.initials: PJ
authors.lastname: Hayes
authors.forename: V J
authors.initials: VJ
authors.lastname: Bender
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D007700:Kinetics; D008969:Molecular Sequence Data; D010196:Pancreatic Elastase / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D014325:Tromethamine / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D010455:Peptides; D014325:Tromethamine; D010196:Pancreatic Elastase