title: Determination of the chirality of amino acid residues in the course of subtractive Edman degradation of peptides.
abstract: A chiral reagent, 1-fluoro-2,4-dinitro-5-L-alanine, was synthesized for the analysis of enantiomeric mixtures of amino acids after precolumn derivatization. The resulting diastereomers can be separated and quantitated by microbore RP-HPLC. These derivatives are relatively stable under the conditions used for acid hydrolysis of peptide bonds. Thus, this reagent was included in the protocol of a subtractive Edman degradation procedure of peptides to determine the sequence position of amino acid residues with concomitant identification of their chirality at a nanomolar level.
authors.affiliation: Dipartimento di Scienze Biochimiche A. Rossi Fanelli, Università La Sapienza, Rome, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Scaloni
authors.forename: M
authors.initials: M
authors.lastname: Simmaco
authors.forename: F
authors.initials: F
authors.lastname: Bossa
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D008969:Molecular Sequence Data; D010455:Peptides / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D010455:Peptides; C072786:1-fluoro-2,4-dinitrophenyl-5-alanine; D010649:Phenylalanine