Ionization constants and solubility of compounds involved in enzymatic synthesis of aminopenicillins and aminocephalosporins

Bioprocess and Biosystems Engineering

Volumn 34, Issue 9, 2011, Pages 1103-1117

  Kurochkina, V B ^a   Sklyarenko, A V ^a   Satarova, J E ^a   Yarotsky, S V ^a  

^a STATE RESEARCH INSTITUTE OF GENETICS AND SELECTION OF INDUSTRIAL MICROORGANISMS   (Russian Federation)

Author keywords

Aminocephalosporins; Aminopenicillins; Enzymatic synthesis; Ionization constants

Indexed keywords

ACID-BASE POTENTIOMETRIC TITRATIONS; ACYLATING AGENTS; AMINOCEPHALOSPORINS; AMINOPENICILLINS; AMOXICILLIN; CEPHALEXIN; D-(-)-P-HYDROXYPHENYLGLYCINE; ENZYMATIC SYNTHESIS; EXPERIMENTAL DATA; EXPERIMENTAL DETERMINATION; IONIZATION CONSTANT; IONIZATION CONSTANTS; REACTION MIXTURE;

AMIDES; BYPRODUCTS; IONIZATION; SYNTHESIS (CHEMICAL); TITRATION; VOLTAMMETRY;

SOLUBILITY;

AMINOCEPHALOSPORIN DERIVATIVE; AMINOPENICILLIN; AMOXICILLIN; AMPICILLIN; BETA LACTAMASE; CEFACLOR; CEFADROXIL; CEFALEXIN; CEFALOGLYCIN; CEFATRIZINE; CEFPROZIL; CEPHALOSPORIN DERIVATIVE; OXFENICINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SYNTHESIS; IONIZATION; MATHEMATICAL MODEL; PH; POTENTIOMETRIC TITRATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

AMINO ACIDS; BETA-LACTAMS; CEPHALOSPORINS; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; ELECTROLYTES; HYDROGEN-ION CONCENTRATION; IONS; MODELS, CHEMICAL; MODELS, THEORETICAL; PENICILLANIC ACID; PENICILLINS; SOLUBILITY; TEMPERATURE; THERMODYNAMICS;

EID: 81755184341     PISSN: 16157591     EISSN: 16157605     Source Type: Journal    
DOI: 10.1007/s00449-011-0560-9     Document Type: Article

References (27)

1. G Volpato RC Rodriges R Fernandez-Lafuente 2010 Use of enzymes in production of semi-synthetic penicillins and cephalosporins: drawbacks and perspectives Curr Med Chem 17 3855 3873 10.2174/092986710793205435 1:CAS:528:DC%2BC3cXhsVGqu7vE
2. Kurochkina VB, Sklyarenko AV (2008) Enzymatic synthesis of beta-lactam antibiotics. Analytical review. In: Zaikov GE (ed) Biotechnology state of the art and prospects for development, Chapter 20. Nova Science Publishers, pp 175-204
3. MI Youshko LM van Langen E de Vroom F van Rantwijk RA Sheldon VK Svedas 2001 Highly efficient synthesis of ampicillin in "aqueous solution-precipitate" system. Repetitive addition of substrates in semi-continuous process Biotechnol Bioeng 73 426 430 10.1002/bit.1076 1:CAS:528:DC%2BD3MXjslWhurc%3D (Pubitemid 32493238)
4. MI Youshko LM van Langen E de Vroom F van Rantwijk RA Sheldon VK Svedas 2002 Penicillin acylase-catalyzed ampicillin synthesis using a pH gradient: a new approach to optimization Biotechnol Bioeng 78 589 593 10.1002/bit.10234 1:CAS:528:DC%2BD38XjvV2mtbY%3D (Pubitemid 34727953)
5. MI Youshko HM Moody AL Bukhanov WHJ Boosten VK Svedas 2004 Penicillin acylase-catalyzed synthesis of β-lactam antibiotics in highly condensed aqueous systems: beneficial impact of kinetic substrate supersaturation Biotechnol Bioeng 85 323 329 10.1002/bit.10863 1:CAS:528:DC%2BD2cXhsVWjsbw%3D (Pubitemid 38182225)
6. MPA Ribeiro ALO Fereira RLC Giordano RC Giordano 2005 Selectivity of the enzymatic synthesis of ampicillin by E.coli PGA in the presence of high concentrations of substrates J Mol Catal B Enzym 33 81 86 10.1016/j.molcatb. 2005.03.003 1:CAS:528:DC%2BD2MXkt1altLg%3D (Pubitemid 40723605)
7. A Basso P Spizzo M Toniutti C Ebert P Linda L Gardossi 2006 Kinetically controlled synthesis of ampicillin and cephalexin in highly condensed systems in the absence of a liquid aqueous phase J Mol Catal B Enzym 39 105 111 10.1016/j.molcatb.2006.01.029 1:CAS:528:DC%2BD28Xjs1Khsr8%3D
8. A Illanes L Wilson O Corrotea L Tavernini F Zamorano C Aguirre 2007 Synthesis of cephalexin with immobilized penicillin acylase at very high substrate concentrations in fully aqueous medium J Mol Catal B Enzym 47 72 78 10.1016/j.molcatb.2007.04.003 1:CAS:528:DC%2BD2sXmtVeis7c%3D (Pubitemid 46819158)
9. A Illanes L Wilson C Aguirre 2009 Synthesis of cephalexin in aqueous medium with carrier-bond and carrier-free penicillin acylase biocatalyst Appl Biochem Biotechnol 157 98 110 10.1007/s12010-008-8255-7 1:CAS:528: DC%2BD1MXhtVChtbrJ
10. Albert A, Serjeant EP (1971) The determination of dissociation constants. Chapman and Hall, London
11. R de Levie 2003 The Henderson-Hasselbalch equation: its history and limitations J Chem Edu 80 146 10.1021/ed080p146
12. T Yamana A Tsuji 1976 Comparative stability of cephalosporins in aqueous solution: kinetics and mechanisms of degradation J Pharmacol Sci 65 1563 1574 10.1002/jps.2600651104 1:CAS:528:DyaE2sXitFOntw%3D%3D
13. A Tsuji E Nakashima T Yamana 1979 Physicochemical properties of amphoteric β-lactam antibiotics II: solubility and dissolution behavior of aminocephalosporins as a function of pH J Pharmacol Sci 68 308 311 10.1002/jps.2600680313 1:CAS:528:DyaE1MXhslCmu7s%3D (Pubitemid 9139720)
14. VK Svedas AL Margolin IV Berezin 1980 Enzymatic synthesis of β-lactam antibiotics: a thermodynamic background Enzym Microbiol Technol 2 138 144 10.1016/0141-0229(80)90070-8 1:CAS:528:DyaL3cXktVKjtbo%3D
15. MF Vieira M Barboza RLC Giordano 2003 Adsorption of components of enzymatic synthesis of ampicillin on different hydrophobic resins Appl Biochem Biotechnol 105-108 705 713 10.1385/ABAB:108:1-3:705 (Pubitemid 36535211)
16. VB Kurochkina PS Nys 2003 Enzymatic synthesis of aminobeta-lactams. Physico-chemical bases of Down-Stream processes Chem Pharm J (Russia) 37 30 37
17. EL Marino A Dominguez-Gil 1981 Determination of the macro- and micro-ionization constants of a dipolar zwitterionic cephalosporin: cefadroxil Int J Pharmacol 8 25 33 10.1016/0378-5173(81)90024-7 1:CAS:528: DyaL3MXks1Ort7g%3D (Pubitemid 11091117)
18. MN Moreno JL Gonzalez MA del Arco J Casado 1990 Determination of macroscopic thermodynamic ionization constants under conditions of variable ionic strength by an optimization algorithm Comput Chem 14 165 168 10.1016/0097-8485(90)80020-3 1:CAS:528:DyaK3cXksVShtr4%3D (Pubitemid 20661267)
19. PS Nys LM Elizarovskaya NN Shellenberg EM Savitskaya 1979 Solubility and complex forming properties of zwitterlites 6-aminocephalosporanic acid and 7-aminodesacetoxycephalosporanic acid Antibiotics 24 895 902 1:CAS:528:DyaL3cXhvVGku7s%3D (Pubitemid 10162221)
20. MS Bulycheva PS Nys EM Savitskaya 1977 Physico-chemical properties of 7-aminoacetoxycephalosporanic acid Antibiotics 22 1073 1076 1:CAS:528: DyaE1cXmsF2isQ%3D%3D
21. PS Nys EV Koltsova NN Shellenberg 1976 Physico-chemical properties of 7-aminodesacetoxycephalosporanic acid Antibiotics 21 391 394 1:CAS:528:DyaE28XksVCru7Y%3D
22. CG Schroen VA Nierstrasz PJ Kroon, et al. 1999 Thermodynamically controlled synthesis of β-lactam antibiotics: equilibrium concentrations and side chain properties Enzym Microbiol Technol 24 489 506 10.1016/S0141-0229(98)00140-9 (Pubitemid 29219586)
23. VB Kurochkina PS Nys 2002 Kinetic and thermodynamic approach to design the processes for enzymatic synthesis of betalactams Biocat Biotrans 20 1 35 41 10.1080/10242420210155 1:CAS:528:DC%2BD38XkvFOqurg%3D (Pubitemid 34177002)
24. PS Nys VB Kurochkina 2000 Methodological approach to development of enzymatic technologies for semisynthetic betalactam antibiotic production Appl Biochem Biotechnol A Enzym Eng Biotechnol 88 221 229 10.1385/ABAB:88:1-3:221 1:CAS:528:DC%2BD3cXnslKksLk%3D
25. Dieter K, Ferhat I (2001) Synthesis of beta-lactam antibiotics with immobilized penicillin amidase. US Patent 6218138
26. Bruggink A (ed) (2001) Synthesis of β-lactam antibiotics: chemistry, biocatalysis and process integration. Kluver Academic Publishers, Dordrecht
27. CGPH Schroen VA Nierstrasz R Bosma, et al. 2002 Integrated reactor concepts for the enzymatic kinetic synthesis of cephalexin Biotechnol Bioeng 80 144 155 10.1002/bit.10348 1:CAS:528:DC%2BD38XnsFKjtr0%3D