Clinical Medicine Research

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Quantum Chemical Modeling of Molecule 6-Aminopenicillanic Acid (6-Apa), of Model of 6-Apa-Phosgene and 6-Apa-Acetyl Chloride

Received: 17 February 2016    Accepted: 17 March 2016    Published: 02 August 2016
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Abstract

For the first time a quantum-chemical method PM3 (Parametric Method 3) in semi empirical approach appreciated geometric and electronic parameters of the new acylated form the molecules 6-APA (6-aminopenicillanic acid), identified patterns of change according to the nature of the acylating agent. In general, the process of acylation of the molecule 6-APA by acylating agents (phosgene and acetyl chloride) leads to much larger changes in new systems of electronic structure than in its spatial structure. In this electronic structure analysis indicates that the acylation of 6-APA of the molecule both acylating agents leads to formation of more stable in the plan hydrolytic cleavage of form of this acid. This fact is a prediction of the characters and is positive for future synthesis of new antibiotics on the basis of 6-APA. Significant absolute value and the sign of the negative enthalpy of formation calculated by PM3, for both systems 6-APA-phosgene 6-APA-acetyl chloride indicate their high thermodynamic stability. The most stable in terms of the thermodynamic system is the 6-APA-acetyl chloride.

DOI 10.11648/j.cmr.s.2016050202.12
Published in Clinical Medicine Research (Volume 5, Issue 2-2, April 2016)

This article belongs to the Special Issue Development of Drugs: Computer Simulation, Chemical Synthesis and Clinical Trials

Page(s) 8-10
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), 2024. Published by Science Publishing Group

Keywords

Semiempirical Quantum Chemical Method, Schrödinger Equation, Parametric Method 3, Modeling, 6-Aminopenicillanic Acid

References
[1] VG Belikov Pharmaceutical Chemistry. In 2 parts: Textbook / V. G. Belikov - 4th edition, revised and enlarged. - M.: MEDpress-Inform, 2007. - 624 p.
[2] Egorov NS Basics of theory of antibiotics. - M.: Medicine, 2004. - 528 p.
[3] Omarova RA, Boshkayeva AK Prospects for the development of research in the development of original drugs // Collection of materials of the International Scientific-Practical Conference. "Pharmacy: Current status, achievements and prospects". - Almaty, 2010 - P. 58-61.
[4] Gribov LA, Mushtakova SP Quantum Chemistry. - M.: Gardariki. - 1999.
[5] Zhidomirov GM, Bagaturyants AA, Abronin IA Applied quantum chemistry. - M.: Chemistry, 1979. - 340 p.
[6] T. Clark Computer chemistry. - M.: Mir, 1990. - 383 p.
[7] Omarova RA, Boshkayeva AK Geometric and electronic characteristics of 6-aminopenicillanic acid and its acetyl derivatives // Abstracts of the 1st All-Russia Scientific Conference "Methods of studying the composition and structure of functional materials", on 11-16 October 2009, Novosibirsk. - P.310.
[8] Omarova RA, Boshkayeva AK, Abdullin KA, Nokerbek Sh Geometric and electronic parameters of the molecule 6-aminopenicillanic acid according to quantum chemical calculations // Abstracts of the XII International scientific conference “Science and education - the leading factor of strategy" Kazakhstan-2030”, Karaganda, 2009.
[9] Omarova RA, Boshkayeva AK Features enzymatic ways of obtaining beta-lactam antibiotics // Collection of materials of the International Scientific-Practical Conference. "Pharmacy: Current status, achievements and prospects". - Almaty, 2010 - P. 25-32.
[10] Omarova RA, Boshkayeva AK Quantum-chemical modeling of the acylation of 6-aminopenicillanic acid // Proceedings of the international scientific-practical conference "Pharmacy: Current status, achievements and prospects". - Almaty, 2010 - P. 144-150.
[11] Boshkayeva AK, Omarova RA, Shakeev SS, Masakbayev AD Isolation of the enzyme penicillin acylase and determination of its activity // Proceedings of the international scientific-practical conference. "Pharmacy: current state, achievements and prospects", devoted to the 80th anniversary of Asfendiyarov Kazakh National Medical University: Almaty, 2011. - P.62-66.
[12] Omarova RA, Boshkayeva AK, Shakeev SS Biotechnological aspects of producing enzymes // “Family Health Century - XXİ century”. Proceedings of the XV International Scientific Conference, April 30 - 07 May 2011, Torremolinos, Spain. P. 85-87.
Author Information
  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

  • Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan

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  • APA Style

    А. К. Boshkayeva, R. A. Omarova, A. S. Kozhamzharovа, А. D. Masakbayev, L. Kiyekbayeva, et al. (2016). Quantum Chemical Modeling of Molecule 6-Aminopenicillanic Acid (6-Apa), of Model of 6-Apa-Phosgene and 6-Apa-Acetyl Chloride. Clinical Medicine Research, 5(2-2), 8-10. https://doi.org/10.11648/j.cmr.s.2016050202.12

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    ACS Style

    А. К. Boshkayeva; R. A. Omarova; A. S. Kozhamzharovа; А. D. Masakbayev; L. Kiyekbayeva, et al. Quantum Chemical Modeling of Molecule 6-Aminopenicillanic Acid (6-Apa), of Model of 6-Apa-Phosgene and 6-Apa-Acetyl Chloride. Clin. Med. Res. 2016, 5(2-2), 8-10. doi: 10.11648/j.cmr.s.2016050202.12

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    AMA Style

    А. К. Boshkayeva, R. A. Omarova, A. S. Kozhamzharovа, А. D. Masakbayev, L. Kiyekbayeva, et al. Quantum Chemical Modeling of Molecule 6-Aminopenicillanic Acid (6-Apa), of Model of 6-Apa-Phosgene and 6-Apa-Acetyl Chloride. Clin Med Res. 2016;5(2-2):8-10. doi: 10.11648/j.cmr.s.2016050202.12

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  • @article{10.11648/j.cmr.s.2016050202.12,
      author = {А. К. Boshkayeva and R. A. Omarova and A. S. Kozhamzharovа and А. D. Masakbayev and L. Kiyekbayeva and G. Ibadullayeva and E. М. Bisenbaev and Z. Olatayeva and Zh. Muhametkan and M. Kudaybergenova and R. Abdykalykov},
      title = {Quantum Chemical Modeling of Molecule 6-Aminopenicillanic Acid (6-Apa), of Model of 6-Apa-Phosgene and 6-Apa-Acetyl Chloride},
      journal = {Clinical Medicine Research},
      volume = {5},
      number = {2-2},
      pages = {8-10},
      doi = {10.11648/j.cmr.s.2016050202.12},
      url = {https://doi.org/10.11648/j.cmr.s.2016050202.12},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.cmr.s.2016050202.12},
      abstract = {For the first time a quantum-chemical method PM3 (Parametric Method 3) in semi empirical approach appreciated geometric and electronic parameters of the new acylated form the molecules 6-APA (6-aminopenicillanic acid), identified patterns of change according to the nature of the acylating agent. In general, the process of acylation of the molecule 6-APA by acylating agents (phosgene and acetyl chloride) leads to much larger changes in new systems of electronic structure than in its spatial structure. In this electronic structure analysis indicates that the acylation of 6-APA of the molecule both acylating agents leads to formation of more stable in the plan hydrolytic cleavage of form of this acid. This fact is a prediction of the characters and is positive for future synthesis of new antibiotics on the basis of 6-APA. Significant absolute value and the sign of the negative enthalpy of formation calculated by PM3, for both systems 6-APA-phosgene 6-APA-acetyl chloride indicate their high thermodynamic stability. The most stable in terms of the thermodynamic system is the 6-APA-acetyl chloride.},
     year = {2016}
    }
    

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    T1  - Quantum Chemical Modeling of Molecule 6-Aminopenicillanic Acid (6-Apa), of Model of 6-Apa-Phosgene and 6-Apa-Acetyl Chloride
    AU  - А. К. Boshkayeva
    AU  - R. A. Omarova
    AU  - A. S. Kozhamzharovа
    AU  - А. D. Masakbayev
    AU  - L. Kiyekbayeva
    AU  - G. Ibadullayeva
    AU  - E. М. Bisenbaev
    AU  - Z. Olatayeva
    AU  - Zh. Muhametkan
    AU  - M. Kudaybergenova
    AU  - R. Abdykalykov
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    JO  - Clinical Medicine Research
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    AB  - For the first time a quantum-chemical method PM3 (Parametric Method 3) in semi empirical approach appreciated geometric and electronic parameters of the new acylated form the molecules 6-APA (6-aminopenicillanic acid), identified patterns of change according to the nature of the acylating agent. In general, the process of acylation of the molecule 6-APA by acylating agents (phosgene and acetyl chloride) leads to much larger changes in new systems of electronic structure than in its spatial structure. In this electronic structure analysis indicates that the acylation of 6-APA of the molecule both acylating agents leads to formation of more stable in the plan hydrolytic cleavage of form of this acid. This fact is a prediction of the characters and is positive for future synthesis of new antibiotics on the basis of 6-APA. Significant absolute value and the sign of the negative enthalpy of formation calculated by PM3, for both systems 6-APA-phosgene 6-APA-acetyl chloride indicate their high thermodynamic stability. The most stable in terms of the thermodynamic system is the 6-APA-acetyl chloride.
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