title: Ionization constants and solubility of compounds involved in enzymatic synthesis of aminopenicillins and aminocephalosporins.
abstract: The article deals with experimental determination of ionization constants and solubility for the compounds (target products, initial β-lactams, acylating agents and by-products) involved in enzymatic synthesis of some therapeutically used aminopenicillins and aminocephalosporins, namely ampicillin, amoxicillin, cephalexin, cephadroxil, cephaloglycin, cefaclor, cefprozil, cefatrizine. Methodology of investigations and the evaluation of experimental data for the determination of ionization constants and solubility of the different type electrolytes are presented. Applications of the methods based on acid-base potentiometric titration and on determination of solubility-pH dependence of assayed substances are discussed. The original data on ionization constants and solubility of amoxicillin, cefprozil, cefatrizine, cephadroxil and initial β-lactams for production of cefaclor, cefprozil and cefatrizine, as well as solubility of by-product D-(-)-p-hydroxyphenylglycine are presented. Experimentally determined parameters and constants available in the literature for all abovementioned aminopenicillins and aminocephalosporins are collected. These data might be used for choice of the conditions of both processes: the enzymatic synthesis and the isolation of the product from reaction mixture.
authors.affiliation: State Research Institute of Genetics and Selection of Industrial Microorganisms (GosNIIgenetika), 1st Dorozhny proezd, 1, Moscow, 117545, Russia.
authors.forename: V B
authors.initials: VB
authors.lastname: Kurochkina
authors.forename: A V
authors.initials: AV
authors.lastname: Sklyarenko
authors.forename: J E
authors.initials: JE
authors.lastname: Satarova
authors.forename: S V
authors.initials: SV
authors.lastname: Yarotsky
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002511:Cephalosporins / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D004573:Electrolytes; D006863:Hydrogen-Ion Concentration; D007477:Ions; D008956:Models, Chemical; D008962:Models, Theoretical; D010397:Penicillanic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D010406:Penicillins / Q000737:chemistry*; D012995:Solubility; D013696:Temperature; D013816:Thermodynamics; D047090:beta-Lactams / Q000737:chemistry
chemical_list: D000596:Amino Acids; D002511:Cephalosporins; D004573:Electrolytes; D007477:Ions; D010406:Penicillins; D047090:beta-Lactams; D010397:Penicillanic Acid; C004408:aminopenicillanic acid