title: The structure-activity relationship of the papain hydrolysis of N-benzoylglycine esters.
abstract: The relationship between structure and the Michaelis-Menten constants (Km) for the papain hydrolysis of a series of 37 N-benzoylglycine esters was investigated. The series studied comprises a wide range of aromatic and aliphatic esters with a 5000-fold variation in their Km constants and essentially constant kcat values. It was found that the variation in the Km constants could be rationalized by the following quantitative structure-activity relationship (QSAR): log 1/Km = 8.13F + 0.33Z + 1.27II3' + 1.95. In this equation F is the field inductive parameter, II3' is the hydrophobic constant for the more lipophilic of the two possible meta substituents and Z is the Van der Waals distance from oxygen through the end of the molecule, in the direction of the 4 position of the aromatic ester moiety.
authors.affiliation: Department of Chemistry, Pomona College, Claremont, CA 91711.
authors.forename: C M
authors.initials: CM
authors.lastname: Compadre
authors.forename: C
authors.initials: C
authors.lastname: Hansch
authors.forename: T E
authors.initials: TE
authors.lastname: Klein
authors.forename: R
authors.initials: R
authors.lastname: Langridge
mesh_terms: D003198:Computer Simulation; D005998:Glycine / Q000031:analogs & derivatives* / Q000378:metabolism; D006868:Hydrolysis; D007700:Kinetics; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D010206:Papain / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D010206:Papain; D005998:Glycine