title: Water-assisted alkaline hydrolysis of monobactams: a theoretical study.
abstract: A theoretical study of the water-assisted alkaline hydrolysis of 2-azetidinone, 3-formylamino-2-azetidinone and 3-formylamino-2-azetidine-1-sulfonate ion is carried out at the B3LYP/6-31+G* level. The effect of bulk solvent is taken into account using the PCM solvation model while specific solvent effects are represented by the inclusion of an ancillary water molecule along the reaction profile. The calculated free energy barriers in solution are in reasonable agreement with experimental values. The observed substituent effects due to the presence of the 3-formylamino and the SO(3) groups attached to the beta-lactam ring are crucial factors determining the hydrolysis of monobactam antibiotics.
authors.affiliation: Departamento de Química Física y Analítica Universidad de Oviedo C/ Julian Clavería 8, 33006, Oviedo Asturias, Spain.
authors.forename: Natalia
authors.initials: N
authors.lastname: Díaz
authors.forename: Dimas
authors.initials: D
authors.lastname: Suárez
authors.forename: Tomás L
authors.initials: TL
authors.lastname: Sordo
authors.forename: Iñaki
authors.initials: I
authors.lastname: Tuñón
authors.forename: Estanislao
authors.initials: E
authors.lastname: Silla
mesh_terms: D001384:Azetidines / Q000737:chemistry; D006868:Hydrolysis; D006878:Hydroxides / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D008997:Monobactams / Q000737:chemistry*; D012997:Solvents / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D014867:Water / Q000494:pharmacology
chemical_list: C116379:2-azetidinone; D001384:Azetidines; D006878:Hydroxides; D008997:Monobactams; D012997:Solvents; D014867:Water