title: Stereoselective formation of bis(alpha-aminoacyl) esters of 5'-AMP suggests a primitive peptide synthesizing system with a preference for L-amino acids.
abstract: In the biosynthesis of proteins, each amino acid passes from the aminoacyl adenylate to become an amino acid ester and finally a 2' (3') peptidyl ester of the AMP residue at the end of a tRNA. Consequently, the chemistry of protein synthesis is the chemistry of aminoacyl and peptidyl AMP. Our data has revealed properties of 5'-AMP and its esters which should allow the preferential catalytic synthesis of L-amino acid peptides via a bis(2', 3'-aminoacyl) ester intermediate. Results in this paper concern one step in the proposed process and show that preexisting Ac-L-Phe monoester reacts about 2.5-times faster to form diester than preexisting Ac-D-Phe monoester.
authors.affiliation: Department of Biochemistry, University of Alabama, Birmingham.
authors.forename: J C
authors.initials: JC
authors.lastname: Lacey
authors.forename: R D
authors.initials: RD
authors.lastname: Thomas
authors.forename: M P
authors.initials: MP
authors.lastname: Staves
authors.forename: C L
authors.initials: CL
authors.lastname: Watkins
mesh_terms: D000249:Adenosine Monophosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004952:Esters; D007202:Indicators and Reagents; D007536:Isomerism; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides / Q000138:chemical synthesis*; D010649:Phenylalanine / Q000031:analogs & derivatives*
chemical_list: D004952:Esters; D007202:Indicators and Reagents; D010455:Peptides; D000249:Adenosine Monophosphate; D010649:Phenylalanine; C048994:N-acetylphenylalanyl-adenosine monophosphate-anhydride; C044228:N-acetylphenylalanine