Synthesis and Characterization of Fmoc Group Protected Amino Acid Chalcone Conjugates

In this study, a series of dipeptide compounds were synthesized as a result of the reaction of Fmoc group-protected amino acids and amino chalcones with triazine reagent. The structures of the synthesized compounds were characterized by FT-IR, 1H and 13C APT NMR spectroscopy techniques. The electrical behavior of the conjugares was investigated with an impedance analyzer in the frequency range of 1-30 kHz. The variation in dielectric constant, dielectric loss, susceptibility and impedance parameters were investigated as a function of frequency. The dielectric constant of the dipeptides ranges from 7.2 to 8.6.

Keywords:

Dielectrical analysis, amino acid conjugates synthesis,

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Amini, E., Safdari, M. S., Weise, D. R. and Fletcher, T. H. (2019). Pyrolysis kinetics of live and dead wildland vegetation from the Southern United State, Journal of Analytical and Applied Pyrolysis, 142, 104613.
Çalışkan, E., Koran, K., Görgülü, A.O. and Çetin A. (2020). Electrical properties of amino acid substituted novel cinnamic acid compounds. Journal of Molecular Structure, 1222, 128830.
Çalışkan, E., Biryan, F., ve Koran, K. (2021). Dipeptit Kaplı Manyetik Fe3O4 Nanopartikülünün Termal ve Dielektrik Özelliklerinin İncelenmesi. Türk Doğa ve Fen Dergisi, 10(1), 259-268.
Darling, D. A. and Joema, S. E. (2020). Antibacterial activity, optical, mechanical, thermal, and dielectric properties of L-phenylalanine fumaric acid single crystals for biomedical, optoelectronic, and photonic applications. The Journal of Materials Science: Materials in Electronics, 31, 22427–22441.
Davies, J.S., and Hakeem, E. (1984). N-terminal substituent and side-chain influences on the chemical shifts of protons in model dipeptide systems. Journal of the Chemical Society, Perkin Transactions 2, 8, 1387-1392.
Dinesh, P., Renukappa, N.M., and Siddaramaiah. (2010). Impedance and susceptance characterization of multiwalled carbon nanotubes with high density polyethylene-carbon black nanocomposites. Integrated Ferroelectrics, 116, 128–136.
Dzubeck, V., and Schneider, J.P. (2000). One-pot conversion of benzyl carbamates into fluorenylmethyl carbamates. Tetrahedron Letters, 41(51), 9953-9956.
Ilangovan, P., Sakvai, M. S., and Kottur A. B. (2017). Synergistic effect of functionally active methacrylate polymer and ZnO nanoparticles on optical and dielectric properties. Materials Chemistry and Physics, 193, 203–211.
Ilgaz, A., ve Perin, D. (2021). Karbon Nanotüp Katkılı Levha Kalıplama Pestilinin AC Elektriksel İletkenliğinin ve Dielektrik Özelliklerinin İncelenmesi. Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, 10(2), 296-303.
Gurgenc, T. and Biryan, F. (2020). Production, thermal and dielectrical properties of Ag-doped nano-strontium apatite and nano h-BN filled poly(4-(3-(2,3,4-trimethoxyphenyl) acryloyl) phenyl acrylate) composites. Journal of Polymer Research, 27, 194.
Kamiński, Z. J. (1987). 2-Chloro-4,6-dimethoxy-1,3,5-triazine. A New Coupling Reagent for Peptide Synthesis. Synthesis, 10, 917-920
Kurt, A. (2009). Thermal decomposition kinetics of poly(nButMA-b-St) diblock copolymer synthesized by ATRP. Journal of Applied Polymer Science, 114, 624.
Kurt, A., and Kaya, E. (2010). Synthesis, characterization, and thermal degradation kinetics of the copolymer poly(4-methoxybenzyl methacrylate-co-isobornyl methacrylate). Journal of Applied Polymer Science,115, 2359.
Li Y., Cordovez M., and Karbhari V. M. (2003). Dielectric and mechanical characterization of processing and moisture uptake effects in E-glass/epoxy composites. Composites Part B, 34: 383- 390.
Lydia Caroline, M., and Vasudevan, S. (2008). Growth and characterization of an organic nonlinear optical material: L-alanine alaninium nitrate, Materials Letters, 62, 2245–2248.
Murakami, M., Hayashi, M., Tamura, N., Hashino, Y., and Ito, Y. (1996). A new water-compatible dehydrating agent DPTF. Tetrahedron Letters, 37(42), 7541-7544.
Narayan Bhat, M. and Dharmaprakash, S. M. (2002). Growth of nonlinear optical c-glycine crystals. Journal of Crystal Growth, 236, 376–380.
Pethrick R. A. and Hayward D. (2002). Real time dielectric relaxation studies of dynamic polymeric systems. Progress in Polymer Science, 27, 1983-2017.
Ramachandra Raja, C., Gokila, G., Antony Joseph, A. (2009). Growth and spectroscopic characterization of a new organic nonlinear optical crystal: L-Alaninium succinate. Spectrochimica Acta Part A, 72, 753–756.
Ramesh Kumar, G., Gokul S. R., Mohan, R., and Jayavel, R. (2005). Growth and characterization of new nonlinear optical L-threonium acetate single crystals. Journal of Crystal Growth, 283, 193–197.
Ramesh, M., Raju, B., Srinivas, R., Sureshbabu, V.V., Vishwanatha, T.M. and Hemantha, H.P. (2011), Characterization of Nα-Fmoc-protected dipeptide isomers by electrospray ionization tandem mass spectrometry (ESI-MSn): effect of protecting group on fragmentation of dipeptides. Rapid Commun. Mass Spectrom., 25,1949-1958.
Sokoto, M. A., Singh, R., Krishna, B. B., Kumar J., and Bhaskar, T. (2016). Non-isothermal kinetic study of de-oiled seed cake of African star apple (Chrosophyllum albidum) using thermogravimetr, Heliyon, 2, e00172.
Suneetha, N. and Rajan Babu, D. (2018). Spectral, nonlinear, optical and optical limiting properties of l-phenylalanine l-phenylalaninium formate single crystal. Spectrochimica Acta Part A, 203, 147-157.
Yakuphanoglu, F., Yoo, Y.T., and Okutan, M. (2004). An impedance spectroscopy study in poly(butylene adipate) ionomers. Annalen der Physik, 13, 559–568.
Tao, K., Levin, A., Abramovich, L.H. and Gazit, E. (2016). Fmoc-modified amino acids and short peptides: simple bio-inspired building blocks for the fabrication of functional materials. Chemical Society Review, 45, 3935-3953.
Zhang, C., Li, C.J., Zhang, G., Ning, X.J., Li, C.X., Liao, H., and Coddet, C. (2007). Ionic conductivity and its temperature dependence of atmospheric plasma-sprayed yttria stabilized zirconia electrolyte. Materials Science and Engineering B, 137,24-30.