Comparative Evaluation of Effectiveness of Biocatalytic Synthesis and Antibacterial Activity of Known Antibiotics and “Chimeric” Cephalosporin Compounds

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The processes of biocatalytic synthesis of cefamandole and cefazoline, as well as four “chimeric” cephalosporins carrying functional groups of these antibiotics in the C3 or C7 position of β-lactam, were carried out using immobilized cephalosporin-acid synthetase under mild standard conditions. A higher efficiency of biocatalytic acylation of β-lactams with a 1(H)-tetrazolylacetic acid residue compared to acylation with almond acid residue was demonstrated. The chemical structure of the obtained compounds was confirmed using the HPLC–MS method. The possibility of using directly reaction mixtures for evaluating the antibacterial activity of synthesized compounds without isolating the target products was demonstrated. The activity of the obtained cephalosporins against twelve microorganisms belonging to the genera Enterococcus, Acinetobacter, Serratia, Pseudomonas, Staphylococcus and Escherichia was evaluated by diffusion into agar. The activity of synthesized “chimeric” cephalosporins against four microorganisms was found: Escherichia coli VKPM B-6695, Staphylococcus aureus VKPM B-6646, Staphylococcus aureus VKPM B-8171 and Staphylococcus epidermidis VKPM B-12635.

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作者简介

A. Sklyarenko

National Research Center “Kurchatov Institute”

编辑信件的主要联系方式.
Email: ingagrosh@mail.ru
俄罗斯联邦, Moscow

I. Groshkova

National Research Center “Kurchatov Institute”

Email: ingagrosh@mail.ru
俄罗斯联邦, Moscow

N. Gorbunov

National Research Center “Kurchatov Institute”

Email: ingagrosh@mail.ru
俄罗斯联邦, Moscow

A. Vasiliev

National Research Center “Kurchatov Institute”

Email: ingagrosh@mail.ru
俄罗斯联邦, Moscow

A. Kamaev

National Research Center “Kurchatov Institute”

Email: ingagrosh@mail.ru
俄罗斯联邦, Moscow

S. Yarotsky

National Research Center “Kurchatov Institute”

Email: ingagrosh@mail.ru
俄罗斯联邦, Moscow

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2. Fig. 1. Scheme of kinetically controlled synthesis of cephalosporins.

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3. Fig. 2. Accumulation curves of cephalosporins during synthesis using the IECASA biocatalyst: 1 – CFM (7-TMCA_МА), 2 – S-p CFM (7-ACA_МА), 3 – Chimera (TDA_МА), 4 – CEZ (TDA_TzAA), 5 – Sp-CEZ (7-ACA_TzAA), 6 – Chimera (7-TMCA_TzAA). The formulas of cephalosporins are given in Table 2.

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4. Table 1.1

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5. Table 1.2

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6. Table 1.3

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10. Table 1.7

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11. Table 1.8

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15. Table 1.12

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16. Table 1.13

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17. Table 2.1

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18. Table 2.2

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20. Table 2.4

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21. Table 2.5

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22. Table 2.6

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