SOLID-LIQUID EQUILIBRIUM DATA OF AMOXICILLIN AND HYDROXYPHENYLGLYCINE IN AQUEOUS MEDIA

被引:14
作者
Bezerra, I. M. [1 ]
Chiavone-Filho, O. [2 ]
Mattedi, S. [1 ]
机构
[1] Univ Fed Bahia, Escola Politecn, BR-40210630 Salvador, BA, Brazil
[2] Univ Fed Rio Grande do Norte, Dept Engn Quim, BR-59066800 Natal, RN, Brazil
关键词
Amoxicillin; Hydroxyphenylglycine; Solubility; Crystallization; Enzymatic synthesis; SEMISYNTHETIC ANTIBIOTICS; PARTITION-COEFFICIENTS; AMINO-ACIDS; SOLUBILITIES; AMPICILLIN; SYSTEMS; PH;
D O I
10.1590/S0104-66322013000100006
中图分类号
TQ [化学工业];
学科分类号
0817 ;
摘要
The enzymatic synthesis of amoxicillin is catalyzed by Penicillin G Acylase (PGA). As byproducts, hydroxyphenylglycine and alcohol are also formed from hydrolytic reactions and antibiotic synthesis, respectively. The design of this process should be directed to promote the synthesis reaction. At the same time, it is necessary to reduce the hydrolytic reaction of amoxicillin through its crystallization or separation from the reaction medium. This work presents measurements of solid-liquid equilibrium data for amoxicillin and hydroxyphenylglycine in water at different temperatures (283.15 - 298.15 K), pH (5.5 - 7.5) and ethanol composition (0 - 70 wt.%). This information is relevant to determine the conditions that offer the lowest solubility for the antibiotic, favoring its separation and purification. All solubility data were obtained using an analytical method with indirect determination by UV spectroscopy. Ideal thermodynamic modeling was applied to describe the experimental solubility data sets.
引用
收藏
页码:45 / 54
页数:10
相关论文
共 23 条
  • [1] Feasibility of the thermodynamically controlled synthesis of amoxicillin
    Diender, MB
    Straathof, AJJ
    van der Wielen, LAM
    Ras, C
    Heijnen, JJ
    [J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1998, 5 (1-4) : 249 - 253
  • [2] DIELECTRIC-CONSTANTS AND DENSITIES OF AQUEOUS MIXTURES OF 2-ALKOXYETHANOLS AT 25-DEGREES-C
    DOUHERET, G
    PAL, A
    [J]. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1988, 33 (01) : 40 - 43
  • [3] Franco L. F. M., 2012, THESIS U SAO PAULO
  • [4] Franks F., 1973, Water: A Comprehensive Treatise
  • [5] Partition coefficients and solubilities of alpha-amino acids in aqueous 1-butanol solutions
    Gude, MT
    Meuwissen, HHJ
    vanderWielen, LAM
    Luyben, KCAM
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 1996, 35 (12) : 4700 - 4712
  • [6] Evaluation of different enzymes as catalysts for the production of β-lactam antibiotics following a kinetically controlled strategy
    Hernández-Jústiz, O
    Terreni, M
    Pagani, G
    García, JL
    Guisán, JM
    Fernández-Lafuente, R
    [J]. ENZYME AND MICROBIAL TECHNOLOGY, 1999, 25 (3-5) : 336 - 343
  • [7] A simplified perturbed hard-sphere model for the activity coefficients of amino acids and peptides in aqueous solutions
    Khoshkbarchi, MK
    Vera, JH
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 1996, 35 (11) : 4319 - 4327
  • [8] On the solubility of proteins as a function of pH: Mathematical development and application
    Mercier Franco, Luis Fernando
    Pessoa Filho, Pedro de Alcantara
    [J]. FLUID PHASE EQUILIBRIA, 2011, 306 (02) : 242 - 250
  • [9] Effect of pH in the synthesis of ampicillin by penicillin acylase
    Ospina, S
    Barzana, E
    Ramirez, OT
    LopezMunguia, A
    [J]. ENZYME AND MICROBIAL TECHNOLOGY, 1996, 19 (06) : 462 - 469
  • [10] DETERMINATION OF DISSOCIATION CONSTANT (Ka) OF CAPTOPRIL AND NIMESULIDE - ANALYTICAL CHEMISTRY EXPERIMENTS FOR UNDERGRADUATE PHARMACY
    Pereira, Airton Vicente
    Garabeli, Aline Ansbach
    Schunemann, Grazieli Delponte
    Borck, Patricia Cristine
    [J]. QUIMICA NOVA, 2011, 34 (09): : 1656 - 1660