Abstract
In the present work, a theoretical study has been performed targeting essential amino acids (EAA) Histidine, Isoleucine, Leucine, Lysine, Methionine, Phenylalanine, Threonine, Tryptophan, Valine, and predicted their different physical and chemical properties by using computational techniques. Amino acids (AA), a fundamental structural unit of protein are amino and carboxyl-rich compounds having electrophilic and nucleophilic regions in them. The reactivity of AA was determined by computing molecular electrostatic potential (MEP) surfaces, counterplots, dipole moment, band gap, global reactivity parameters, and polarizability parameters. Spectral analysis (UV–Vis, Raman) helps in studying their electronic and vibrational properties. The polarizability and first-order hyperpolarizability parameters were also computed to detect the nonlinear optical (NLO) behavior of AA. The comparison done with reference NLO materials Urea, Phenyl urea, and 3-nitroaniline showed that Phenylalanine has higher hyperpolarizability and can better be used as a potent NLO material.
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References
Akinyele, O.F., Adekunle, A.S., Olayanju, D.S., Oyeneyin, O.E., Durodola, S.S., Ojo, N.D., Aanuoluwapo, A.A., Ajayeoba, T.A., Olasunkanmi, L.O.: Synthesis and corrosion inhibition studies of (E)-3-(2-(4-chloro-2-nitrophenyl)diazenyl)-1-nitrosonaphthalen-2-ol on mild steel dissolution in 0.5 M HCl solution- experimental DFT and monte carlo simulations. J. Mol. Struct. 1268, 133738 (2022). https://doi.org/10.1016/j.molstruc.2022.133738
Bairy, R., Jayarama, A., Kulkarni, S.D., Murari, M.S., Vijeth, H.: Improved nonlinear optical absorption mechanism and susceptibility (Ï(3)) of CdS nanostructured thin films: role of zinc doping. Mater Sci Semicond Process. 121, 105400 (2021). https://doi.org/10.1016/j.mssp.2020.105400
Becke, A.D.: Density-functional thermochemistry III The role of exact exchange. J. Chem. Phys. 98, 5648 (1993). https://doi.org/10.1063/1.464913
Becke, A.D.: Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals. J. Chem. Phys. 107, 8554–8560 (1997). https://doi.org/10.1063/1.475007
Bhatt, H., Pant, T., Dhoundiyal, C.C., Rana, M., Chowdhury, P., Joshi, P.C., Arya, P., Tiwari, H.: Computational study of the intermolecular interactions and their effect on the UV-visible spectra of the ternary liquid mixture of benzene, ethanol and propylene glycol. J Mol Model. 26, 268 (2020). https://doi.org/10.1007/s00894-020-04533-y
Buriahi, A., Singh, M.S., Arslan, V.P.: Gamma-ray attenuation properties of some NLO materials: potential use in dosimetry. Radiat Environ Biophys. 59, 145–150 (2020). https://doi.org/10.1007/s00411-019-00824-y
Cheng, Q., Shi, X., Li, C., Jiang, Y., Shi, Z., Zou, J., Wang, X., Wang, X., Cui, Z.: Chromophores with side isolate groups and applications in improving the poling efficiency of second non-linear optical (NLO) materials. Dyes Pigm. 162, 721–727 (2019). https://doi.org/10.1016/j.dyepig.2018.11.001
Christophersen, O.A., Haug, A.: Animal products diseases and drugs: a plea for better integration between agricultural sciences human nutrition and human pharmacology. Lipids Health Dis. (2011). https://doi.org/10.1186/1476-511X-10-16
Dennington, R., Keith, T., Millam, J.: GaussView Version 412. Semichem, Inc., Shawnee Mission, KS (2007).
Fleck, M., Petrosyan, A.M.: Difficulties in the growth and characterization of non-linear optical materials: a case study of salts of amino acids. J. Cryst. Growth. 312, 2284–2290 (2010). https://doi.org/10.1016/j.jcrysgro.2010.04.054
Frisch, M. J., Trucks, G. W., Schlegel, H. B. et al.: Gaussian 09, Revision B. 01, Gaussian Inc., Wallingford CT. 121, 150–166 (2009).
Huang, X., Braams, B.J., Bowman, J.M.: Ab initio potential energy and dipole moment surfaces of (H2O)2. J. Phys. Chem. a. 110, 445–451 (2006). https://doi.org/10.1021/jp053583d
Idouhli, R., Ousidi, A.N., Khadiri, M.E., Abouelfida, A., Itto, M.Y.A., Auhmani, A., Benyaich, A.: Electrochemical and theoretical studies of some monoterpenic thiazolidinones as corrosion inhibitors for steel in acidic media. J Adhes Sci Technol. 35, 1404–1425 (2021). https://doi.org/10.1080/01694243.2020.1850011
Javier-Hila, A.M.V., Javier, B.C.V., Hila, F.C., Guillermo, N.R.D.: Photon attenuation parameters of non-essential amino acids using EPICS2017 library interpolations. SN Appl. Sci. 3, 542 (2021). https://doi.org/10.1007/s42452-021-04507-6
John, N.L., Abraham, S., Sajan, D., Philip, R., Joy, N., Chitra, R.: Molecular structure, NLO properties and vibrational analysis of l-Histidine tetra fluro borate by experimental and computational spectroscopic techniques. Spectrochim. Acta A Mol. Biomol. Spectrosc. 226, 117615 (2020). https://doi.org/10.1016/j.saa.2019.117615
Khnifira, M., Hamidi, S.E., Mahsoune, A., Sadiq, M., SerdaroÄŸlu, G., Kaya, S., Qourzal, S., Barka, N., Abdennouri, M.: Adsorption of methylene blue cationic dye onto brookite and rutile phases of titanium dioxide: quantum chemical and molecular dynamic simulation studies. Inorg. Chem. Commun. 129, 108659 (2021). https://doi.org/10.1016/j.inoche.2021.108659
King, T.A., Kandemir, J.M., Walsh, S.J., David, R.: Photocatalytic methods for amino acid modification. Chem. Soc. Rev. Spring. 50(1), 39–57 (2021). https://doi.org/10.1039/D0CS00344A
Kirtman, B., Luis, J.M., Bishop, D.M.: Simple finite field method for calculation of static and dynamic vibrational hyperpolarizabilities: curvature contributions. J. Chem. Phys. 108, 10008 (1998). https://doi.org/10.1063/1.476460
Koopmans, T.: About the assignment of wave functions and eigenvalues for the individual electrons in an atom. Physica. 1, 104–113 (1934). https://doi.org/10.1016/S0031-8914(34)90011-2
Krishnakumar, V., Nagalakshmi, R.: Studies on the first-order hyperpolarizability and terahertz generation in 3-nitroaniline. Phys. b: Condens. Matter. 403, 1863–1869 (2008). https://doi.org/10.1016/j.physb.2007.10.341
Kuramochi, H., Aoyama, G., Okajima, H., Sakamoto, A., Kanegawa, S., Sato, O., Takeuchi, S., Tahara, T.: Femtosecond polarization switching in the crystal of a [CrCo] dinuclear complex. Angew. Chem. 132, 15999–16003 (2020). https://doi.org/10.1002/ange.202004583
Lakhera, S., Devlal, K., Ghosh, A., Rana, M..: In silico investigation of phytoconstituents of medicinal herb piper longum against SARS-CoV-2 by molecular docking and molecular dynamics analysis. Res. Chem. (2021). https://doi.org/10.1016/j.rechem.2021.100199
Lakhera, S., Devlal, K., Ghosh, A., Rana, M.: Modelling the DFT structural and reactivity study of feverfew and evaluation of its potential antiviral activity against COVID-19 using molecular docking and MD simulations. Chem. Pap. (2022a). https://doi.org/10.1007/s11696-022-02067-6
Lakhera, S., Rana, M., Devlal, K., Yadav, R., Celik, I.: A comprehensive exploration of pharmacological properties, bioactivities and inhibitory potentiality of luteolin from Tridax procumbens as anticancer drug by in-silico approach. Struct Chem (2022b). https://doi.org/10.1007/s11224-022-01882-7
Lakhera, S., Devlal, K., Rana, M., Dhuliya, V.: Quantum mechanical study of three aromatic bioactive fatty alcohol compounds with nonlinear optical and potential light harvesting properties. Opt. Mater. 129, 112476 (2022c). https://doi.org/10.1016/j.optmat.2022.112476
Lakhera, S., Devlal, K., Rana, M., Celik, I.: Study of nonlinear optical responses of phytochemicals of Clitoria ternatea by quantum mechanical approach and investigation of their anti-Alzheimer activity with in silico approach. Struct Chem (2022d). https://doi.org/10.1007/s11224-022-01981-5
Lee, S.T., Khairul, W.M., Lee, O.J., Rahamathullah, R., Daud, A.I., Halim, K., Bulat, K., Sapari, S., Razak, F.I.A., Krishnan, G.: Electronic, reactivity and third order nonlinear optical properties of thermally-stable push-pull chalcones for optoelectronic interest: experimental and DFT assessments. J. Phys. Chem. Solids. 159, 110276 (2021). https://doi.org/10.1016/j.jpcs.2021.110276
Lopez, M. J., Mohiuddin, S. S.: Biochemistry. Essential Amino Acids. (2022). https://www.ncbi.nlm.nih.gov/books/NBK557845/?report=classic
Marappan, D., Palanisamy, M., Shu, H.M., Balraj, B., Sivakumar, C.: Growth, vibrational, optical, mechanical and DFT investigations of an organic nonlinear optical material – phenylurea. Z. Phys. Chem. 233, 1659–1682 (2019). https://doi.org/10.1515/zpch-2018-1230
Midgley, P., Dunin, P., Borkowski, R.: Electron tomography and holography in materials science. Nature Mater. 8, 271–280 (2009). https://doi.org/10.1038/nmat2406
Moroz, L., Maslovskaya, A.: Fractional differential model of domain boundary kinetics in ferroelectrics. Comput Approach AIP Conference Proc. 2328, 020001 (2021). https://doi.org/10.1063/5.0042140
Muhammad, S., Nakano, M.: Computational strategies for nonlinear optical properties of carbon nano-systems. Nanosci Comput Chem: Res Progress (2013). https://doi.org/10.1201/b16368-10
Muhammad, S., Nakano, M., Al-Sehemi, A.G., Kitagawa, Y., Irfan, A., Chaudhry, A.R., Kishi, R., Ito, S., Yoneda, K., Fukuda, K.: The role of singlet diradical character in carbon nanomaterials: a novel hot spot for efficient nonlinear optical materials. NANOHL (2016). https://doi.org/10.1039/C6NR06097H
Muhammad, S., Xu, H. L., Zhong, R. L., Su, Z. M., Al Sehemic, A. G.: A. Irfan, Quantum chemical design of nonlinear optical materials by sp2 -hybridized carbon nanomaterials: issues and opportunities. J. Mater. Chem. C. 1, 5439–5449 (2013). https://doi.org/10.1039/c3tc31183j.
Naseema, K., Sreedharan, R., Ravi, S., Raghi, K.R., Kumar, M.: Experimental and computational studies on optical properties of a promising N-benzylideneaniline derivative for non-linear optical applications. Z. Naturforsch. 75, 557–573 (2020). https://doi.org/10.1515/zna-2020-0047
Nazrin, S.N., Halimah, M.K., Muhammad, F.D.: Comparison study of optical properties on erbium-doped and silver-doped zinc tellurite glass system for non-linear application. J. Mater. Sci: Mater. Electron. 30, 6378–6389 (2019). https://doi.org/10.1007/s10854-019-00940-x
Ojo, N.D., Krause, R.W., Egbedi, N.O.O.: Electronic and nonlinear optical properties of 2-(((5-aminonaphthalen-1-yl)imino)methyl)phenol: experimental and time-dependent density functional studies. J. Mol. Liq. 319, 114157 (2020). https://doi.org/10.1016/j.molliq.2020.114157
Oyeneyin, O.E., Ojo, N.D., Ipinloju, N., James, A.C., Agbaffa, E.B.: Investigation of corrosion inhibition potentials of some aminopyridine schiff bases using density functional theory and monte carlo simulation. Chemistry Africa 5, 319–332 (2022). https://doi.org/10.1007/s42250-021-00304-1
Pathade, S., Jagdale, B.: Experimental and computational investigations on the molecular structure vibrational spectra electronic properties FMO and MEP analyses of 46-Bis(4-Fluorophenyl)-56-dihydropyrimidin-2(1H)-one: A DFT Insight. Phys. Chem. Res. (2020). https://doi.org/10.22036/pcr.2020.227546.1763.
Prettre, G., Pullman, G.: Quantum mechanical calculations of NMR chemical shifts in nucleic acids. Q. Rev. Biophys. 20, 113–172 (1987). https://doi.org/10.1017/S0033583500004169
Rana, M., Chowdhury, P.: Nonlinear optical responses of organic based indole derivative: an experimental and computational study. Mater. Today: Proc. 28(1), 241–245 (2020). https://doi.org/10.1016/j.matpr.2020.01.598
Rana, M., Singla, N., Chatterjee, A., Shukla, A., Chowdhury, P.: Investigation of nonlinear optical (NLO) properties by charge transfer contributions of amine functionalized tetraphenylethylene. Opt. Mater. 62, 80–89 (2016). https://doi.org/10.1016/j.optmat.2016.09.043
Rana, M., Singla, N., Pathak, A., Dhanya, A., Narayana, C., Chowdhury, P.: Vibrational-electronic properties of intra/inter molecular hydrogen bonded heterocyclic dimer: an experimental and theoretical study of pyrrole-2-carboxaldehyde. Vib. Spectrosc. 89, 16–25 (2017). https://doi.org/10.1016/j.vibspec.2016.12.003
Rana, M., Chatterjee, A., Chowdhury, P.: Investigation of nonlinear optical properties of organic based di amine substituted tetraphenylethylene. AIP Conf. Proc. 2009, 020055 (2018). https://doi.org/10.1063/1.5052124
Rana, M., Jain, A., Rani, V., Chowdhury, P.: Glutathione capped core/shell CdSeS/ZnS quantum dots as a medical imaging tool for cancer cells. Inorg. Chem. Commun. 112, 107723 (2020). https://doi.org/10.1016/j.inoche.2019.107723
Rana, M., Pooja, Chowdhury, P., Investigation on nonlinear optical responses of different pyrrole derivatives: a computational study. AIP Conf. Proc. (2019). https://doi.org/10.1063/1.5120919.
Ray, P.C.: Size and shape dependent second order nonlinear optical properties of nanomaterials and their applications in biological and chemical sensing. Chem. Rev 110, 5332–5365 (2010). https://doi.org/10.1021/cr900335q
Saito, K., Mitsuhashi, K., Ishikita, H.: Dependence of the chlorophyll wavelength on the orientation of a charged group: why does the accessory chlorophyll have a low site energy in photosystem II? J. Photochem. Photobiol. 402, 112799 (2020). https://doi.org/10.1016/j.jphotochem.2020.112799
Senthilkumar, S., Seralathan, J., Muthukumaran, G.: Synthesis, structure analysis, biological activity and molecular docking studies of some hydrazones derived from 4-aminobenzohydrazide. J. Mol. Struct. 1226, 129354 (2021). https://doi.org/10.1016/j.molstruc.2020.129354
Sheikhi, M., Shahab, S., Alnajjar, R., Ahmadianarog, M.: Adsorption properties of the new anti-cancer drug alectinib on CNT (6,6–6) nanotube: geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, Excited State), FMO, MEP and HOMO–LUMO investigations. J Clust Sci. 30, 83–96 (2019). https://doi.org/10.1007/s10876-018-1460-9
Soares, J.D.P., Scott, H.L., Teixeira, F.J., Gustavo, P.D.: Dietary amino acids and immunonutrition supplementation in cancer-induced skeletal muscle mass depletion: a mini-review curr. Pharm. Des. 26, 970–978 (2020). https://doi.org/10.2174/1381612826666200218100420
Swartling, D. J., Coonce, J. G., Cashman, D. J.: Using balloons to model pi-conjugated systems and to teach frontier molecular orbital theory. World J. Chem. Educ. 6, 102–106 (2018). https://doi.org/10.12691/wjce-6-2-5.
Then, A., Mácha, K., Ibrahim, B.: A novel method for achieving an optimal classification of the proteinogenic amino acids. Sci Rep. 10, 15321 (2020). https://doi.org/10.1038/s41598-020-72174-5
Ullah, F., Kosar, N., Ali, A., Maria, Mahmood, T., Ayub, K.: Alkaline earth metal decorated phosphide nanoclusters for potential applications as high performance NLO materials: a first principle study. Phys. E: Low-Dimens. Syst. Nanostructures. (2020). https://doi.org/10.1016/j.physe.2019.113906.
Visscher, K.M., Geerke, D.P.: Deriving Force-field parameters from first principles using a polarizable and higher order dispersion model. J. Chem. Theory Comput. 15, 1875–1883 (2019). https://doi.org/10.1021/acs.jctc.8b01105
Wang, H., Xi, Q., Liang, P., Zheng, L., Hong, Y., Zuo, Y.: IHEC_RAAC: an online platform for identifying human enzyme classes via reduced amino acid cluster strategy. Amino Acids 53, 239–251 (2021). https://doi.org/10.1007/s00726-021-02941-9
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Lakhera, S., Rana, M. & Devlal, K. Theoretical study on spectral and optical properties of essential amino acids: a comparative study. Opt Quant Electron 54, 714 (2022). https://doi.org/10.1007/s11082-022-04118-4
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DOI: https://doi.org/10.1007/s11082-022-04118-4