Gamma irradiated of amino acid derivatives examined by EPR and Simulation Methods

Öz

Amino acids of solid state DL-beta-amino-n-butyric acid (BABA), Triethylene tetramine hexa acetic acid (TTHAA) and DL-Asparagine monohydrate (DLAMH) have been investigated by Electron Paramagnetic Resonance Spectroscopy. Free radicals formed in irradiated powder crystals have been examined at temperatures of 300 Kelvin. The structure of the free radical and the hyperfine structure constants were reported. The free radicals formed in the compounds were found to be stable for three months, fifteen days and two months respectively. The obtained results are in agreement with the literature values.

Anahtar Kelimeler

• Electron Paramagnetic Rezonance
• Gamma Irradiation
• Free radicals
• amino acid

Gama Işınları ile Işınlanmış Amino Asit Türevlerinin EPR ve Simulasyon Metodu ile İncelenmesi

Öz

Katı durumdaki DL-beta-amino-n-butirik asit, Trietilen terami hekza asedik asit ve DL-asparagin monohidrat aminoasitleri Elektron paramanyetik rezonans spektroskopisi ile incelendi. Işınlanmış toz kristallerde oluşan serbest radikaller 300 Kelvin sıcaklıklarında incelendi. Serbest radikalin yapısı ve aşırı ince yapı sabitleri tespit edildi. Bileşiklerde oluşan serbest radikallerin sırasıyla 3 ay, 15 gün ve 2 ay boyunca stabil olduğu görüldü. Elde edilen sonuçlar literatür değerleri ile uyumludur.

Anahtar Kelimeler

• Elektron Paramanyetik Rezonans
• Gama Işınlaması
• Serbest Radikaller
• Amino Asit

Kaynakça

1. Guo, X.; Chang, C.; Lam, E.Y., Blind separation of electron paramagnetic resonance signals using diversity minimization, J. Mag. Reson., 2010, 204(1):26-36.
2. Swartz, H.M.; Bolton, J.R.; Borg, D.C., Biological Applications of Electron Spin Resonance, Wiley, New York, 1972.
3. Ogawa, M.; Ishigure, K.; Oshima, K., ESR study of irradiated single crystals of amino acids—I: Glutamic acid and glutamic acid hydrochloride, Radiat. Phys. Chem., 1980, 16(4): 281-287.
4. Salih, N.A.; Eid, O.I.; Benetis, N:P.; Lindgren, M.; Lund, A.; Sagstuen, E., Reversible conformation change of free radicals in X-irradiated glutarimide single crystals studied by ENDOR, J. Chem. Phys, 1996, 212: 409-419.
5. Aydın, M.; Osmanoğlu, Y.E., EPR study of free radicals in amino acids derivatives irradiated by gamma rays, Romanian J. Phys., 2011, 56(9): 1156-1161.
6. Sinclair, J., ESR study of irradiated glycine at low temperatures, J. Chem. Phys., 1971, 55(2): 245-251.
7. Poupko, R.; Loewenstein, A., Electron spin resonance study of radicals derived from simple amines and amino acids, Silver, B.L.; J. Am. Chem. Soc., 1971, 93(3): 580-586.
8. Taniguchi P. H., Fukui, K; Ohnishi S.;, Hatano, H., Hasagewa, H.; Maruyama, T., Free-radical intermediates in the reaction of the hydroxyl radical with amino acids, J. Phys. Chem, 1968, 72(6): 1926-1931.

9. Shields, H.; Hamrick, P.; Delaigle, D., Electron Spin Resonance of X‐Irradiated Valines, J. Chem. Phys., 1967, 46: 3649-3652.
10. Bešić, E., EPR study of the free radicals in the single crystals of 2-thiothymine γ-irradiated at 300 K, J. Mol. Struct, 2009, 917(2-3): 71-75.
11. Osmanoglu, Ş.; Köksal, F.; Kartal, I.; Ucun, F., Electron paramagnetic resonance of gamma-irradiated single crystals of two isobutyric acid derivatives, Radiat. Phys. Chem., 1997, 49(4): 419-420.
12. Başkan M.H.; Osmanoglu Ş., EPR of Gamma Irradiated Nα-Monochloroacetyl-α-Aminoisobutyric Acid, Z. Naturforch, 2004, 59a: 665-668.
13. Osmanoğlu Ş.; Başkan, M.H, EPR of Gamma Irradiated Single Crystals of N-Acetyl- andN-Carbamyl-α-Aminoisobutyric Acid Z.Naturforsch, 2003, 58a: 290-292.
14. Box, H.C.; Freund, H.G.; Budzunski E.E., Paramagnetic Absorption of Irradiated Glycine, J. American Chem. Society, 1966, 88(4): 658-661.
15. Köksal F.; Osmanoğlu, Ş., Electron paramagnetic resonance of gamma irradiation damage centres in ethylenediaminetetraacetic and diethylenediaminepentaacetic acids, J Chem Research, 1993 (2):84-85.
16. Osmanoğlu, Y.E.; Sütçü, K., EPR studies of the free radicals generated in gamma irradiated amino acid derivatives, J. Mol. Struct, 2017, 1145: 240–243.
17. Strzelczak, G.; Berges, J.; Houee-Levin, C.; Pogocki, D.; Bobrowski, K., EPR spectroscopy and theoretical study of γ-irradiated asparagine and aspartic acid in solid state, Biophys. Chem, 2007, 125(1): 92-103.
18. Close, D.M.; Fouse, G.W.; Bernhard, W.A., ESR and ENDOR study of single crystals of L‐asparagine⋅H2O x‐irradiated at room temperature, J.Chem. Phys., 1977, 66(4): 1534.
19. Hwang, BK.; JY. Sunwoo, J.Y.; Kim, YJ.; Kim B.S., Accumulation of β-1,3-glucanase and chitinase isoforms, and salicyclic acid in the DL-β-amino-n-butyric acid-induced resistance response of pepper stems to Phytophthora capsici. Physiological and Molecular Plant Pathology, 1997, 51(5): 305-322.
20. Özgönen H.; Erkılıç A., Phytophthora Blight (Phytophthora capsici Leonian) Control in Pepper by Salicylic Acid and Beta Amino Butyric Acid and Disease Resistance Mechanism, J. Turk. Phytopath., 2007, 36: 1-19.
21. Yordanov N.D., Is our knowledge about the chemical and physical properties of DPPH enough to consider it as a primary standard for quantitative EPR spectrometry, Appl. Mag. Res.1996, 10: 339–350.
22. McKelvey, R.D., Journal of Chemical Education, 1987, 64: 479
23. Aydın, M., EPR investigation of gamma-irradiated iminodiacetic and amino acid derivatives, Bulgarian Chemical Communications, 2010, 42(3): 232–235.
24. Başkan, M.H.; Aydın, M.; Osmanoğlu, Ş., Investigation of 60Co γ-irradiated L-(-) malic acid, N-methyl-DL-valine and L-glutamic acid γ-ethyl ester by electron paramagnetic resonance technique, Journal of Molecular Structure, 2010, 983(1-3): 200–202.
25. Başkan, M.H.; Aydın, M., Electron paramagnetic resonance studies of gamma-irradiated DL-alanine ethyl ester hydrochloride, L-theanine and L-glutamic acid dimethyl ester hydrochloride, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013, 112: 280–282.
26. Şimşek, R.; Gündüz, M.G.; Şafak, C.; Kökpınar, Ö.; Aydın, M., Free radicals properties of some gamma-irradiated organic compounds, Bulgarian Chemical Communications, 2017, 49(1): 82 – 86
27. Wood D. E.; Liyod, R.V., EPR of Free Radicals in an Adamantane Matrix. I. Aliphatic Aminoalkyl Radicals, J. Chem. Phys.,1970, 53(10): 3932.
28. Aydın, M.; Osmanoğlu, Y.E.; Başkan,M.H., Electron paramagnetic resonance of γ-irradiated glycyl-L-glutamine monohydrate, iminodiacetic acid and methyliminodiacetic acid, Radiation Effects and Defects in Solids, 2008, 163(1): 47-53.
29. Aydın, M.;. Başkan, M.H.; Yakar, S.; Ulak, F.Ş.; Aydınol, M.; Aydınol, B.; Büyüm,M., EPR studies of gamma-irradiated L-alanine ethyl ester hydrochloride, L-arginine and alanyl-L-glutamine, Radiation Effects and Defects in Solids, 2008, 163(1) :41-46.
30. Aydın, M.;. Başkan, M.H.; Osmanoğlu, Y.E., EPR Study of Gamma Induced Radicals in Amino and Iminodiacetic Acid Derivatives, Brazilian Journal of Physics, 2009, 39(3): 583-586.
31. Aydın, M., EPR study of free radicals in amino acid derivatives gamma-irradiated at 300 K, Indian Journal of Pure & Applied Physics, 2010, 48(9): 611-614.