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Synthesis, crystal structures, and theoretical studies on bio-pertinent disulfides derived from methyl thiosalicylate and furan-2-thiocarboxylic acid and their interaction with native human lysozymes

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Abstract

Aromatic substituted thiol and aromatic 2-furoylthiocarboxylic acid were catalytically oxidized into corresponding disulfides, dimethyl 2,2'-disulfanediyldibenzoate (1) and furan-2-carboxylic dithioperoxyanhydride (3) have been characterized by single crystal X-ray analysis. Methylene insertion (gas phase) into the disulfide linkage was studied in both molecules. We have performed extensive docking studies of the interaction with Native Human Lysozyme and found that 3 exhibits better binding efficiencies with Native Human Lysozyme compared to compound 1. Hirshfeld analyses were made to study the type of weak interactions quantitatively. The thermal and electronic stabilities of these compounds have been studied using Density functional theory calculations. Natural bond orbital analyses have been used to find out hyper-conjugative energies, highest occupied molecular orbitals- Lowest unoccupied molecular orbital along with electronic transitions. We have also investigated the thermal stabilities of molecules as well as the vibrational contribution in the thermodynamic parameters such as specific heat, Gibb’s free energy, and entropy at different temperatures.

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Funding

KK and SB are thankful to UGC [JRF/SRF Award no. 20/12/2015 (ii) EU-V], and the IoE faculty grants of Banaras Hindu University (Scheme number: 6031) for funding. SG thanks SERB/DST/IoE (BHU) for the financial support.

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Authors and Affiliations

  1. Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India

    Krishna Kumar, Rajesh Pratap, Somenath Garai & Subrato Bhattacharya

  2. Department of Physics, Institute of Science, Banaras Hindu University, Varanasi, 221005, India

    Anil Kumar Vishwkarma & Amit Pathak

  3. Department of Rasa Shastra and Bhaishajya Kalpana, Faculty of Ayurveda, Institute of Medical Science, Banaras Hindu University, Varanasi, 221005, India

    Rohit Sharma

Authors
  1. Krishna Kumar
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  2. Anil Kumar Vishwkarma
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  3. Rajesh Pratap
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  4. Somenath Garai
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  5. Amit Pathak
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  7. Subrato Bhattacharya
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Contributions

Conceptualization, writing—original draft, Synthesis: KK, SB; Thermal analysis: AKV; Writing, editing: AP, SG; Editing: SB. All authors have reviewed and approved the final version of the manuscript prior to submission.

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Correspondence to Subrato Bhattacharya.

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Kumar, K., Vishwkarma, A.K., Pratap, R. et al. Synthesis, crystal structures, and theoretical studies on bio-pertinent disulfides derived from methyl thiosalicylate and furan-2-thiocarboxylic acid and their interaction with native human lysozymes. Chem. Pap. 78, 3721–3733 (2024). https://doi.org/10.1007/s11696-024-03342-4

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