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Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide

Received: 11 March 2023     Accepted: 10 July 2023     Published: 24 July 2023
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Abstract

Background: The reported rise in drug-resistant bacteria, as well as the prevalence of oxidative stress-related disorders, motivated the need for novel antimicrobial and antioxidants activity. The synthesis of gly-gly based dipeptides bearing sulphonamide functionalities is reported. Methodology: The base promoted reaction of appropriate substituted benzenesulphonyl chloride with L-glycine afforded compounds (3a-3b) and the condensation reaction of (3a-3b) with carboxamide derivatives gave the targeted products (7a-7b) using peptide coupling reagent. The characterization of compounds was done using 1HNMR, 13CNMR, FTIR and HRMS. Results: In the in vitro antimicrobial activity, compounds 7a (MIC 6.10 mg/mL), 7ai (MIC 7.01 mg/mL), 7b (MIC 7.42 mg/mL), 7bi (MIC 6.32 mg/mL) was most potent against S. aureus, B. subtilis, P. aeruginosa and E. coli respectively. Compounds 7a (MIC 6.90 mg/mL) and 7b (MIC 6.48 mg/mL) were most active against C. Albicans and A. Niger respectively. Compound 7a and 7bi (85.00% and 88.78% at 25mg/mL) exhibits excellent percentage inhibition antioxidant activities comparable with vitamin C (90.78% at 25mg/mL) and alsocompound 7bi had the best IC50 values of 0.7674 mg/mL. Conclusion: The synthesized compounds were found to be potent antibacterial, antifungal and antioxidant agents.

Published in American Journal of Applied Scientific Research (Volume 9, Issue 3)
DOI 10.11648/j.ajasr.20230903.14
Page(s) 109-114
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2023. Published by Science Publishing Group

Keywords

Synthesis, Benzenesulphonamide, Dipeptide, Antimicrobial Activity, Antifungal Activity, Antioxidant Activity

References
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    Ike Ozoemena Christian, Okoro Uchechukwu Christopher, Aguoma Chinedu Chris, Orjioke Nwakaego Marytheresa, Ugwu David Izuchukwu, et al. (2023). Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide. American Journal of Applied Scientific Research, 9(3), 109-114. https://doi.org/10.11648/j.ajasr.20230903.14

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    ACS Style

    Ike Ozoemena Christian; Okoro Uchechukwu Christopher; Aguoma Chinedu Chris; Orjioke Nwakaego Marytheresa; Ugwu David Izuchukwu, et al. Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide. Am. J. Appl. Sci. Res. 2023, 9(3), 109-114. doi: 10.11648/j.ajasr.20230903.14

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    AMA Style

    Ike Ozoemena Christian, Okoro Uchechukwu Christopher, Aguoma Chinedu Chris, Orjioke Nwakaego Marytheresa, Ugwu David Izuchukwu, et al. Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide. Am J Appl Sci Res. 2023;9(3):109-114. doi: 10.11648/j.ajasr.20230903.14

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  • @article{10.11648/j.ajasr.20230903.14,
      author = {Ike Ozoemena Christian and Okoro Uchechukwu Christopher and Aguoma Chinedu Chris and Orjioke Nwakaego Marytheresa and Ugwu David Izuchukwu and Nweloke Regina Chinyere and Orie Kingsley John and Nsude Okechukwu Paul and Okoye Nebeolisa Johnson and Eze Cosmos Chibuike and Attah Solomon Izuchukwu and Ugwu Michael Chukwuemeka},
      title = {Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide},
      journal = {American Journal of Applied Scientific Research},
      volume = {9},
      number = {3},
      pages = {109-114},
      doi = {10.11648/j.ajasr.20230903.14},
      url = {https://doi.org/10.11648/j.ajasr.20230903.14},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajasr.20230903.14},
      abstract = {Background: The reported rise in drug-resistant bacteria, as well as the prevalence of oxidative stress-related disorders, motivated the need for novel antimicrobial and antioxidants activity. The synthesis of gly-gly based dipeptides bearing sulphonamide functionalities is reported. Methodology: The base promoted reaction of appropriate substituted benzenesulphonyl chloride with L-glycine afforded compounds (3a-3b) and the condensation reaction of (3a-3b) with carboxamide derivatives gave the targeted products (7a-7b) using peptide coupling reagent. The characterization of compounds was done using 1HNMR, 13CNMR, FTIR and HRMS. Results: In the in vitro antimicrobial activity, compounds 7a (MIC 6.10 mg/mL), 7ai (MIC 7.01 mg/mL), 7b (MIC 7.42 mg/mL), 7bi (MIC 6.32 mg/mL) was most potent against S. aureus, B. subtilis, P. aeruginosa and E. coli respectively. Compounds 7a (MIC 6.90 mg/mL) and 7b (MIC 6.48 mg/mL) were most active against C. Albicans and A. Niger respectively. Compound 7a and 7bi (85.00% and 88.78% at 25mg/mL) exhibits excellent percentage inhibition antioxidant activities comparable with vitamin C (90.78% at 25mg/mL) and alsocompound 7bi had the best IC50 values of 0.7674 mg/mL. Conclusion: The synthesized compounds were found to be potent antibacterial, antifungal and antioxidant agents.},
     year = {2023}
    }
    

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  • TY  - JOUR
    T1  - Synthesis, Antimicrobial and Antioxidant Properties of Gly-Gly Based Dipeptide
    AU  - Ike Ozoemena Christian
    AU  - Okoro Uchechukwu Christopher
    AU  - Aguoma Chinedu Chris
    AU  - Orjioke Nwakaego Marytheresa
    AU  - Ugwu David Izuchukwu
    AU  - Nweloke Regina Chinyere
    AU  - Orie Kingsley John
    AU  - Nsude Okechukwu Paul
    AU  - Okoye Nebeolisa Johnson
    AU  - Eze Cosmos Chibuike
    AU  - Attah Solomon Izuchukwu
    AU  - Ugwu Michael Chukwuemeka
    Y1  - 2023/07/24
    PY  - 2023
    N1  - https://doi.org/10.11648/j.ajasr.20230903.14
    DO  - 10.11648/j.ajasr.20230903.14
    T2  - American Journal of Applied Scientific Research
    JF  - American Journal of Applied Scientific Research
    JO  - American Journal of Applied Scientific Research
    SP  - 109
    EP  - 114
    PB  - Science Publishing Group
    SN  - 2471-9730
    UR  - https://doi.org/10.11648/j.ajasr.20230903.14
    AB  - Background: The reported rise in drug-resistant bacteria, as well as the prevalence of oxidative stress-related disorders, motivated the need for novel antimicrobial and antioxidants activity. The synthesis of gly-gly based dipeptides bearing sulphonamide functionalities is reported. Methodology: The base promoted reaction of appropriate substituted benzenesulphonyl chloride with L-glycine afforded compounds (3a-3b) and the condensation reaction of (3a-3b) with carboxamide derivatives gave the targeted products (7a-7b) using peptide coupling reagent. The characterization of compounds was done using 1HNMR, 13CNMR, FTIR and HRMS. Results: In the in vitro antimicrobial activity, compounds 7a (MIC 6.10 mg/mL), 7ai (MIC 7.01 mg/mL), 7b (MIC 7.42 mg/mL), 7bi (MIC 6.32 mg/mL) was most potent against S. aureus, B. subtilis, P. aeruginosa and E. coli respectively. Compounds 7a (MIC 6.90 mg/mL) and 7b (MIC 6.48 mg/mL) were most active against C. Albicans and A. Niger respectively. Compound 7a and 7bi (85.00% and 88.78% at 25mg/mL) exhibits excellent percentage inhibition antioxidant activities comparable with vitamin C (90.78% at 25mg/mL) and alsocompound 7bi had the best IC50 values of 0.7674 mg/mL. Conclusion: The synthesized compounds were found to be potent antibacterial, antifungal and antioxidant agents.
    VL  - 9
    IS  - 3
    ER  - 

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Author Information
  • Department of Industrial Chemistry, Enugu State University of Science and Technology, Enugu, Nigeria

  • Department of Pure and Industrial Chemistry, University of Nigeria Nsukka, Enugu, Nigeria

  • Department of Industrial Chemistry, Enugu State University of Science and Technology, Enugu, Nigeria

  • Department of Science Laboratory and Technology, University of Nigeria Nsukka, Enugu, Nigeria

  • Department of Pure and Industrial Chemistry, University of Nigeria Nsukka, Enugu, Nigeria

  • Department of Pure and Industrial Chemistry, University of Nigeria Nsukka, Enugu, Nigeria

  • Department of Pure and Industrial Chemistry, University of Port Harcourt, Port Harcourt, Nigeria

  • Department of Industrial Chemistry, Enugu State University of Science and Technology, Enugu, Nigeria

  • Department of Pure and Industrial Chemistry, University of Nigeria Nsukka, Enugu, Nigeria

  • Natural Science Unit, Enugu, Department of Pure and Industrial Chemistry, University of Nigeria Nsukka, Nigeria

  • Department of Pure and Industrial Chemistry, University of Nigeria Nsukka, Enugu, Nigeria

  • Department of Medical Laboratory Science, Nnamdi Azikiwe University, Nnewi, Nigeria

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