Biomaterial Database

Mechanistic features of pepsin-catalyzed amino transfer reactions. 1980

M S Silver, and S L James

Peptic cleavage of N-trifluoroacetyl-L-tryptophan (CF3CO-Trp) at pH 2.45 to 5.4 in the presence of L-beta-phenyllactic acid (Pla) yields much PlaTrp. Formation of PlaTrp represents a typical peptic amino transfer reaction. In this instance PlaTrp undoubtedly derives from a reaction between the acceptor, Pla, and the carboxylate anion, CF3CO-TrpCOOO- (or a species obtained from it). This observation suggests that in general the anionic form of a substrate, such as AcPheTrpCOOO- in the case of AcPheTrp, may be the primary source of the amino acid residue transferred in amino transpeptidations. Other evidence supports the validity of the proposal. Furthermore it has the virtue of rationally explaining why AcPheTrpNH2-like substrates fail to participate in amino transpeptidations and why these reactions tend to increase in importance at high pH.

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D009842	Oligopeptides	Peptides composed of between two and twelve amino acids.	Oligopeptide
D010434	Pepsin A	Formed from pig pepsinogen by cleavage of one peptide bond. The enzyme is a single polypeptide chain and is inhibited by methyl 2-diaazoacetamidohexanoate. It cleaves peptides preferentially at the carbonyl linkages of phenylalanine or leucine and acts as the principal digestive enzyme of gastric juice.	Pepsin,Pepsin 1,Pepsin 3
D002851	Chromatography, High Pressure Liquid	Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed.	Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D006863	Hydrogen-Ion Concentration	The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH	pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D000595	Amino Acid Sequence	The order of amino acids as they occur in a polypeptide chain. This is referred to as the primary structure of proteins. It is of fundamental importance in determining PROTEIN CONFORMATION.	Protein Structure, Primary,Amino Acid Sequences,Sequence, Amino Acid,Sequences, Amino Acid,Primary Protein Structure,Primary Protein Structures,Protein Structures, Primary,Structure, Primary Protein,Structures, Primary Protein
D013379	Substrate Specificity	A characteristic feature of enzyme activity in relation to the kind of substrate on which the enzyme or catalytic molecule reacts.	Specificities, Substrate,Specificity, Substrate,Substrate Specificities