Study on benzylpenicillin lactim zwitterion conformations.
Journal name: World Journal of Pharmaceutical Research
Original article title: Am1 study on the conformations of zwitterions of benzylpenicillin lactim tautomer
The WJPR includes peer-reviewed publications such as scientific research papers, reports, review articles, company news, thesis reports and case studies in areas of Biology, Pharmaceutical industries and Chemical technology while incorporating ancient fields of knowledge such combining Ayurveda with scientific data.
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Summary of article contents:
Introduction
Benzylpenicillin, a broad-spectrum antibiotic, plays a crucial role in the treatment of various infections caused by gram-positive organisms. Despite its clinical importance, it often undergoes tautomerism and presents instability in aqueous solutions. This study focuses on the conformational and electronic properties of benzylpenicillin lactim tautomer and its zwitterionic forms using the semi-empirical AM1 method. A central component of the research is to understand the factors influencing proton transfer and the stability of different conformations of zwitterions in solution.
Importance of Zwitterions in Chemical Properties
Zwitterions of benzylpenicillin lactim tautomer are essential due to their increased polarity and stability across various pH ranges. The study reveals that the formation of zwitterions occurs by the transfer of protons to specific nitrogen atoms, effectively altering the charge distribution within the molecule. The energies of frontier molecular orbitals (E_HOMO and E_LUMO) were analyzed, demonstrating the viability of electron transitions which hint at the photochemical reactivity of the zwitterionic forms. This protonation behavior also correlates to the molecule's dipole moment, indicating the influence of charge distribution on molecular reactivity.
The Role of Computational Methods
The research utilized the AM1 (Austin Model 1) method to optimize the conformational and electronic structure of benzylpenicillin lactim tautomer and its zwitterions. The computational approach provided insights into the heats of formation, ionization potential, and dipole moments of the studied compounds. Full optimization calculations yielded the lowest energy conformations, demonstrating how conformational analysis through computational chemistry can elucidate the structural complexities and stability of molecular forms, especially for compounds exhibiting tautomerism.
Conformational Changes and Their Effects
Conformational analysis highlighted how molecular deformations affect the stability and reactivity of zwitterions. The study notes that different zwitterionic forms arise from distinct proton transfer pathways, which modify the dihedral angles and inherent molecular geometry. The energetics associated with these conformational changes suggest that proton transfer and structural rearrangement are pivotal to understanding the reaction dynamics of benzylpenicillin lactim tautomer. These modifications lead to significant changes in the stability of zwitterionic states, with proton affinities varying among nitrogen sites.
Conclusion
The AM1 calculations in this study emphasize the significance of zwitterions of benzylpenicillin lactim tautomer, revealing their non-planar geometries and dominance of proton transfer at specific nitrogen sites. The interactions with polar solvents, leading to hydrogen bonding, are crucial for understanding the equilibria between zwitterionic forms in solution. Overall, this research sheds light on the interplay between molecular conformation, electronic properties, and environmental factors, underscoring the importance of theoretical methods in predicting the behavior and stability of complex pharmaceutical compounds.
Original source:
This page is merely a summary which is automatically generated hence you should visit the source to read the original article which includes the author, publication date, notes and references.
Dasari Chandrasekhar Rao and Bojja Rajeshwar Rao
World Journal of Pharmaceutical Research:
(An ISO 9001:2015 Certified International Journal)
Full text available for: Am1 study on the conformations of zwitterions of benzylpenicillin lactim tautomer
Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research
Doi: 10.20959/wjpr201710-9386
Download the PDF file of the original publication
FAQ section (important questions/answers):
What is the significance of benzylpenicillin in therapy?
Benzylpenicillin is a broad-spectrum antibiotic used to treat various infections, including those of the respiratory tract, skin, urinary tract, and more, primarily against gram-positive organisms.
What method was used to optimize the zwitterions of benzylpenicillin?
The study employed the AM1 semi-empirical molecular orbital method to optimize and calculate the conformation and electronic structure of the zwitterions in the gas phase.
How do zwitterions form in benzylpenicillin lactim tautomer?
Zwitterions form through proton transfer between oxygen and nitrogen atoms, resulting in different protonation states and conformations of the molecule, which influence its electronic properties.
What affects the stability of benzylpenicillin zwitterions?
The stability of zwitterions is influenced by their conformational structure, electronic properties, and the polarity of the solvent in which they are solubilized.
What are the electric properties analyzed in benzylpenicillin?
The study analyzed properties like heats of formation, dipole moments, and frontier molecular orbital energies (E HOMO and E LUMO) for the benzylpenicillin lactim tautomer and its zwitterions.
What conclusions were made about zwitterion stability and conformation?
Zwitterions exhibit nearly non-planar geometry, with N12 as the primary protonation site, highlighting the importance of solvent polarity on zwitterion stability and conformation.
Glossary definitions and references:
Scientific and Ayurvedic Glossary list for “Study on benzylpenicillin lactim zwitterion conformations.”. This list explains important keywords that occur in this article and links it to the glossary for a better understanding of that concept in the context of Ayurveda and other topics.
1) Calculation:
Calculation refers to the mathematical process of determining values based on formulas or models. In the context of the research, it is fundamental for optimizing molecular structures and predicting electronic properties using the AM1 method. Calculations help in understanding the stability, reactivity, and behavior of zwitterions.
2) Table:
A table is a systematic arrangement of data in rows and columns. In the context of the study, tables present critical numerical data such as heats of formation, dipole moments, and atomic charges. This structured format allows for easy comparison and visualization of results, enhancing comprehension of complex information.
3) Kakatiya:
Kakatiya refers to Kakatiya University, located in Warangal, India, which is the institution where the research was conducted. This geographical and institutional identification lends credibility to the study, indicating that it was carried out within a recognized academic environment and reflects regional scientific contributions.
4) Medium:
Medium denotes the surrounding environment in which interactions occur. In this study, it refers to the solvent's effect on zwitterion behavior and equilibrium. The choice of medium influences molecular stability and reactivity, providing insights into how chemical properties change based on solvation and polarity.
5) India:
India is the country where the research was conducted, particularly referencing Kakatiya University. The mention highlights the geographical context of the study, underscoring the global collaboration in scientific research and showcasing the advancements and contributions in chemistry from Indian institutions.
6) Study (Studying):
Study represents the systematic investigation into the conformations and properties of benzylpenicillin lactim tautomer and its zwitterions. This term underscores the research's purpose, which is to explore molecular behaviors, optimize structures, and analyze electronic characteristics through advanced computational methods.
7) Arrangement:
Arrangement refers to the spatial organization of atoms within a molecule. In this research, it pertains to the conformations of the benzylpenicillin lactim tautomer and zwitterions. Understanding the arrangement is crucial for predicting chemical reactivity and interactions, especially in complex molecules with functional groups.
8) Nature:
Nature pertains to the intrinsic characteristics and properties of substances studied. In this research, it refers to the physical and chemical aspects of benzylpenicillin and its zwitterions. Recognizing the nature of these compounds aids in understanding their behavior in biological systems and their interaction with various targets.
9) Sign:
Sign denotes an indication or meaning drawn from scientific observations or data. In the context of the study, signs can refer to the electronic characteristics indicated by calculated dipole moments or charges. Identifying signs is key to interpreting the results and understanding their implications for drug design.
10) Chemotherapy:
Chemotherapy refers to the treatment of disease by the administration of drugs designed to inhibit or kill pathogens or cancer cells. Penicillins, including benzylpenicillin, play a vital role in chemotherapy, particularly for bacterial infections. The study underscores the relevance of understanding drug properties in therapeutic contexts.
11) Antibiotic (Antibacterial):
An anti-biotic is a type of medication used to prevent or treat bacterial infections. Benzylpenicillin is a prime example, acting against a range of gram-positive bacteria. Its classification as an antibiotic highlights the study's relevance to pharmacology and the development of effective treatments for infections.
12) Discussion:
Discussion denotes the interpretation and analysis of research results. In this study, it emphasizes the evaluation of findings related to the conformations and electronic properties of zwitterions. This section is critical for understanding the implications of the data and for placing the research within the broader scientific context.
13) Warangal:
Warangal is the city in India where Kakatiya University is located and where the research was conducted. Mentioning Warangal situates the study geographically, contributing to local academic identity and institutions specializing in pharmaceutical and chemical research, thus highlighting regional contributions to science.
14) Activity:
Activity refers to the biological effectiveness or physiological effect of a compound. In this research, it relates to the pharmacological action of benzylpenicillin and how its structure and molecular properties influence its ability to bind to targets and exert therapeutic effects in patients.
15) Channel:
Channel typically refers to structures or pathways through which substances move. In the study, it pertains to porin channels in bacterial membranes that affect the selective permeability to antibiotics like benzylpenicillin. Understanding channel interactions is essential for drug design and determining a compound's efficacy.
16) Dasari:
Dasari refers to Dasari Chandrasekhar Rao, one of the authors of the study. Mentioning the author's name acknowledges their contribution to the research, showcasing individual expertise and credibility in the field of chemistry and molecular modeling, essential for establishing the validity of the findings.
17) Field:
Field refers to a specific area of study or research. In this context, it pertains to quantum chemistry and computational methods used for molecular analysis. Identifying the field provides insight into the scientific disciplines engaged in the research, highlighting the interplay of theory and practical applications in chemistry.
18) Bile:
Bile relates to the digestive fluid produced by the liver that helps in fat digestion and absorption. In the context of this study, the mention of bile emphasizes the relevance of benzylpenicillin's applicability in various infections, including those affecting the bile tract, thus linking the research to clinical implications.