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

А. К. Boshkayeva; R. A. Omarova; A. S. Kozhamzharovа; А. D. Masakbayev; L. Kiyekbayeva; G. Ibadullayeva; E. М. Bisenbaev; Z. Olatayeva; Zh. Muhametkan; M. Kudaybergenova; R. Abdykalykov

doi:doi:10.11648/j.cmr.s.2016050202.12

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

А. К. Boshkayeva, R. A. Omarova, A. S. Kozhamzharovа, А. D. Masakbayev, L. Kiyekbayeva, G. Ibadullayeva, E. М. Bisenbaev, Z. Olatayeva, Zh. Muhametkan, M. Kudaybergenova, R. Abdykalykov

Published in Clinical Medicine Research (Volume 5, Issue 2-2)

Received: 17 February 2016 Accepted: 17 March 2016 Published: 2 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.

Published in	Clinical Medicine Research (Volume 5, Issue 2-2) This article belongs to the Special Issue Development of Drugs: Computer Simulation, Chemical Synthesis and Clinical Trials
DOI	10.11648/j.cmr.s.2016050202.12
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), 2016. Published by Science Publishing Group

Keywords

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

References

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[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.

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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://article.sciencepublishinggroup.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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TY  - JOUR
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
Y1  - 2016/08/02
PY  - 2016
N1  - https://doi.org/10.11648/j.cmr.s.2016050202.12
DO  - 10.11648/j.cmr.s.2016050202.12
T2  - Clinical Medicine Research
JF  - Clinical Medicine Research
JO  - Clinical Medicine Research
SP  - 8
EP  - 10
PB  - Science Publishing Group
SN  - 2326-9057
UR  - https://doi.org/10.11648/j.cmr.s.2016050202.12
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.
VL  - 5
IS  - 2-2
ER  -

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Author Information

А. К. Boshkayeva

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
R. A. Omarova

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
A. S. Kozhamzharovа

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
А. D. Masakbayev

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
L. Kiyekbayeva

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
G. Ibadullayeva

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
E. М. Bisenbaev

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
Z. Olatayeva

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
Zh. Muhametkan

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
M. Kudaybergenova

Pharmaceutical Faculty, Asfendiyarov Kazakh National Medical University, Almaty, Republic of Kazakhstan
R. Abdykalykov

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

Copy | Download

@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://article.sciencepublishinggroup.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}
}

Copy | Download

TY  - JOUR
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
Y1  - 2016/08/02
PY  - 2016
N1  - https://doi.org/10.11648/j.cmr.s.2016050202.12
DO  - 10.11648/j.cmr.s.2016050202.12
T2  - Clinical Medicine Research
JF  - Clinical Medicine Research
JO  - Clinical Medicine Research
SP  - 8
EP  - 10
PB  - Science Publishing Group
SN  - 2326-9057
UR  - https://doi.org/10.11648/j.cmr.s.2016050202.12
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.
VL  - 5
IS  - 2-2
ER  -

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