Chemical Reactivity Descriptors and Molecular Docking Studies of Octyl 6-O-hexanoyl-β-D-glucopyranosides

Authors

  • Naimul Islam Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, 4331, Bangladesh https://orcid.org/0000-0003-4335-9323
  • Mohammad H.O. Roshid Department of Anesthesia and Intensive Care, Chattogram Medical College, Chittagong, 4203, Bangladesh
  • Md. Lutfor Rahaman Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong, 4331, Bangladesh https://orcid.org/0000-0001-9897-1267

DOI:

https://doi.org/10.33736/jaspe.3727.2021

Keywords:

COVID-19, n-Octyl β-D-glucopyranoside (OBG), Docking, Potential drugs

Abstract

The present study describes different chemical reactivity predictions of 6-O-hexanoylation of octyl β-D-glucopyranosides prepared from octyl β-D-glucopyranoside (OBG). Also, molecular docking of the OBGs was conducted against SARS-CoV-2 main protease (6LU7), urate oxidase (Aspergillus flavus; 1R51) and glucoamylase (Aspergillus niger; 1KUL). DFT optimization indicated that glucoside 1 and its ester derivatives 2-7 exist in 4C1 conformation with C1 symmetry. Interestingly, the addition of ester group(s) decreased the HOMO-LUMO gap (Δԑ) of glucosides indicating their good chemical reactivities, whereas the other chemical reactivity descriptors indicated their moderate reactive nature. This fact of moderate reactivity was confirmed by their molecular docking with 6LU7, 1R51 and 1KUL. All the esters showed a moderate binding affinity with these three proteins. More importantly, incorporation of the ester group(s) increased binding affinity with 6LU7 and 1R51, whereas decreased with 1KUL as compared to non-ester OBG 1.

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Journal of Applied Science & Process Engineering, Volume 8, Number 2, 2021

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2021-10-31

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Islam, N., Roshid, M. H., & Rahaman, M. L. (2021). Chemical Reactivity Descriptors and Molecular Docking Studies of Octyl 6-O-hexanoyl-β-D-glucopyranosides. Journal of Applied Science &Amp; Process Engineering, 8(2), 903–912. https://doi.org/10.33736/jaspe.3727.2021

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Vol. 8 No. 2 (2021): Journal of Applied Science & Process Engineering, Volume 8, Number 2, 2021

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