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Quantum chemical analysis of isomerization and protonation of amino group in D-glucosamine

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Abstract

D-glucosamine (GluN) is a vital amino monosaccharide present in bio-polymers like chitin and chitosan. Using density functional theory (DFT), we examined its molecular and structural properties in different conformations and protonation states. Results revealed the β-form as more stable than the α-form when neutral. Protonation led to shorter hydrogen bond distances with improved interactions. Frontier molecular orbital analysis showed the amino group's significant role in influencing HOMO and LUMO orbitals based on protonation. The calculated energy gap (ΔE) indicated protonated D-glucosamine’s higher stability and lower reactivity compared to neutral isomers. These findings enhance our comprehension of D-glucosamine’s in bio-polymers applications.

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The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Acknowledgments

To Roberto López Rendón†, your legacy will live on through the years. The author is gratefully for the computing time granted by the Supercomputer Hybrid Cluster “Xiuhcoatl” at General Coordination of Information and Communications Technologies (CGSTIC) of Cinvestav-IPN. This research/thesis was partially supported by the NLHPC supercomputing infrastructure (ECM-02).

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Authors and Affiliations

  1. Transdisciplinary Research for Drug Discovery, Sociedad Mexicana de Epigenética y Medicina Regenerativa A. C. (SMEYMER), Mexico City, Mexico

    Rodolfo Daniel Ávila-Avilés

  2. Laboratory of Epigenetics of Skeletal Muscle Regeneration, Department of Genetics and Molecular Biology, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional (CINVESTAV), Mexico City, Mexico

    Rodolfo Daniel Ávila-Avilés

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Ávila-Avilés, R.D. Quantum chemical analysis of isomerization and protonation of amino group in D-glucosamine. MRS Communications 13, 1303–1308 (2023). https://doi.org/10.1557/s43579-023-00455-x

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