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Title: Density functional theory calculations of electronic properties and bioactivity of natural macromolecule N-β-D-Glucopyranosyl Vincosamide (C32H40N2O14) showing activity against the diabetic mellitus and prediction of its derivative
Authors: Mishra, Ashok Kumar
Gupta, Vimlesh
Keywords: Biomolecule;DFT;ONIOM Model;HOMO-LUMO;NLO;Chemical reactivity
Issue Date: Mar-2020
Publisher: NISCAIR-CSIR, India
Abstract: Optimized structure, (NMR, UV-Vis and IR) spectral characteristics, highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), molecular electrostatic potential surface (MESP), global reactivity descriptors using density functional theory (DFT) approach; the non-linear optical (NLO) properties, local reactivity descriptors and natural bond orbital (NBO) analysis using Multi layer ONIOM model have been studied on the title molecule which is a reported plant-derived  showing activity against diabetic mellitus and its derivative namely  N,alpha-L-rhamnopyranosyl Vincosamide has also been predicted. The result shows that self consistent field energy at its optimized geometry is -1509756.99 kcal/mol, peak value of IR active vibration at 1134 cm-1, theoretical (1H&13C) NMR chemical shifts along with UV-visible absorption peak observed at 289.60 nm are in good agreement with their experimental counterparts and the first order hyperpolarizability is 21029.66×10-33esu which is 61.26 times greater than that of Urea revealing that this molecule is viable for NLO applications. The HOMO- LUMO energy gap is reasonably small ≈-0.14194a.u which makes this molecule soft for chemical reaction. Its MESP surface has been found to be reactive site suited for drug activity wherein the electrophilic region is located around 23O-atom. Local reactivity descriptors reveal that the 24C-atom of ring in title molecule is more prone to the electrophilic attack. NBO analysis indicates that donor level (O23) π →π*(C18-N22) acceptor level interaction corresponds to the highest stabilization energy E(2)≈ 24.47 Kcal/mol associated with electron delocalization. A comparative report of the free energy of binding of the title molecule and its predicted derivative with the various protein receptors calculated via molecular docking approach has also been presented in this paper. The present study forms the theoretical basis for exploring the bioactivity and predicting the derived-structure of natural biomolecules using quantum chemical computations.
Page(s): 61-79
ISSN: 2581-8198 (Online)
Appears in Collections:AIR Vol.02(1) [March 2020]

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