Synthesis and Characterization of Fmoc Group Protected Amino Acid Chalcone Conjugates

Year 2022, Volume: 11 Issue: 3, 155 - 159, 29.09.2022

Eray Çalışkan

https://doi.org/10.46810/tdfd.1165708

Abstract

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

References

• 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.