Amide bond formation by applying thermal shock and rapid identification of the products using ion mobility spectrometry

Subject Areas :

farshad  mirzaee valadi ¹ (گروه شیمی، دانشکده علوم، دانشگاه زنجان، زنجان، ایران)
Hamed  Bahrami ² (aDepartment of Chemistry, University of Zanjan, Zanjan 45371-38791, Iran)
Manijeh  Tozihi ³ (Assistant Prof. in Physical Chemistry, Department of Chemistry, University of Zanjan, Zanjan, Iran)

Received: 2021-06-16 Accepted : 2021-06-16 Published : 2021-05-22

Keywords: Thermal Shock, Ion mobility spectrometry, Amide bond formation, Perindopril erbumine,

Abstract :

The amide bond constitutes the skeleton of biologically significant peptides and proteins. The amide group exists in many pharmaceutical compounds. Thus, the development of an efficient amidation method continues to be an essential scientific pursuit. In this research, a simple method was introduced for the direct and solvent-free formation of amides, and also for real-time product identification. At first, the ion mobility spectrum of perindopril erbumine salt was obtained, and the ionic species resulting from evaporation and ionization of this salt in corona discharge were identified. Subsequently, the formation of a product ion having heavier mass than protonated perindopril was demonstrated by applying thermal shock at 400 °C to perindopril erbumine salt. The variation of the intensities of the peaks in the ion mobility spectra over the elapsed time, and also predicting the mass of the ionic species were examined to determine the nature of the newly formed product. Through the method described in this article the new product was identified to be an amide compound. The efficiency of the two-reference method for applying the mass-mobility correlation equation to predict the masses of ion species in the ion mobility spectrometry was demonstrated. The results of this study showed that applying thermal shock to perindopril erbumine in addition to degradation of the sample can cause to create new products through the formation of amide bond.

References:

[1] Ghose, A.K.; Viswanadhan, V.N.; Wendoloski, J.J.; J. Comb. Chem. 1, 55-68, 1999.

[2] Houlding, T.K.; Tchabanenko, K.; Rahman, M.T.; Rebrov, E.V.; Org. Biomol. Chem. 11, 4171-4177, 2013.

[3] Gelens, E.; Smeets, L.; Sliedregt, L.A.; Van Steen, B.J.; Kruse, C.G.; Leurs, R.; Orru, R.; Tetrahedron let. 46, 3751-3754, 2005.

[4] Wang, X.J., Yang, Q., Liu, F., You, Q.; ‎Synth. Commun. 38, 1028-1035, 2008.

[5] Lundberg, H.; Tinnis, F.; Adolfsson, H.; Chem. Eur. J. 18, 3822-3826, 2012.

[6] Deiana, C.; Sakhno, Y.; Fabbiani, M.; Pazzi, M.; Vincenti, M.; Martra, G.; ChemCatChem. 5, 2832-2834, 2013.

[7] Lundberg, H.; Adolfsson, H.; ACS Catal. 5, 3271-3277, 2015.

[8] Krause, T.; Baader, S.; Erb, B.; Gooßen, L.J.; Nat. Commun. 7, 11732, 2016.

[9] Liu, Y.; Cherkasov, N.; Gao, P.; Fernández, J.; Lees, M.R.; Rebrov, E.V.; J. Catal. 355, 120-130, 2017.

[10] Mirza-Aghayan, M.; Tavana, M.M.; Boukherroub, R.; Ultrason. Sonochem. 29, 371-379, 2016.

[11] de Figueiredo, R.M.; Suppo, J.-S.; Campagne, J.-M.; Chem. Rev. 116, 12029-12122, 2016.

[12] Goossen, L.J.; Ohlmann, D.M.; Lange, P.P; Synth. 2009, 160-164, 2009.

[13] Eiceman, G.A.; Crit. Rev. Anal. Chem. 22, 471-490, 1991.

[14] Bahrami, H.; Farrokhpour, H.; Spectrochim. Acta A 135, 646-651, 2015.

[15] Forbes, T.P.; Lawrence, J.; Verkouteren, J.R.; Verkouteren, R.M.; Analyst 144, 6391-6403, 2019.

[16] Zheng, X.; Wojcik, R.; Zhang, X.; Ibrahim, Y.M.; Burnum-Johnson, K.E.; Orton, D.J.; Annu. Rev. Anal. Chem. 10, 71-92, 2017.

[17] Rearden, P., Harrington, P.B.; Anal. Chim. Acta 545, 13-20, 2005.

[18] Shahraki, H.; Tabrizchi, M.; Farrokhpour, H.; J. Hazard. Mater. 357, 1-9, 2018.

[19] Hernández-Mesa, M.; Ropartz, D.; García-Campaña, A.M.; Rogniaux, H.; Dervilly-Pinel, G.; Le Bizec, B.; Molecules 24, E2706, 2019.

[20] Bahrami, H.; Salehabadi, H.; J. Mol. Struct. 1083, 330-335, 2015.

[21] Valadbeigi, Y.; Farrokhpour, H.; Rouholahnejad, F.; Tabrizchi, M.; Int. J. Mass Spectrom. 369, 105-111, 2014.

[22] Jazan, E.; Tabrizchi, M.; Chem. Phys. 355, 37-42, 2009.

[23] Baumbach, J.I.; Eiceman, G.A.; Appl. spectrosc. 53, 338A-355A, 1999.

[24] Parker, E.; Aarons, L.; Rowland, M.; Resplandy, G.; Eur. J. Pharm. Sci. 26, 104-113, 2005.

[25] Ferrari, R.; Expert Rev. Cardiovasc. Ther. 3, 15-29, 2005.

[26] Hurst, M.; Jarvis, B.; Drugs 61, 867-896, 2001.

[27] Fogari, R.; Pasotti, C.; Zoppi, A.; Corradi, L.; Mugellini, A.; Preti, P.; J. Hypertens. 22, S173, 2004.

[28] Remko, M; Eur. J. Med. Chem., 44, 101-108, 2009.

[29] Remko, M.; Bojarska, J.; Ježko, P.; Sieroń, L.; Olczak, A.; Maniukiewicz, W.; J. Mol. Struct. 997, 103-109, 2011.

[30] Guharay, S.K.; Dwivedi, P.; Hill, H.H.; IEEE Trans. Plasma Sci. 36, 1458-1470, 2008.

[31] Tabrizchi, M.; Khayamian, T.; Taj, N.; Rev. Sci Instrum. 71, 2321-2328, 2000.

[32] Bahrami, H.; Farajmand, B.; Lakmehsari, M.S.; Int. J. Mass Spectrom. 430, 110-116, 2018.

[33] Tozihi, M.; Bahrami, H.; Farajmand, B.; Tabrizchi, M.; Int. J. Mass Spectrom. 448, 116272-116284, 2020.

[34] Marlton, S.J.P.; McKinnon, B.I.; Ucur, B.; Maccarone, A.T.; Donald, W.A.; Blanksby S.J.; Trevitt, A.J.; Faraday Discuss. 217, 453-475, 2019.

[35] Valadbeigi, Y.; Bayat, S.; Ilbeigi, V.; Anal. Chem. 92, 7924–7931, 2020.

[36] Carroll, D.I.; Dzidic, I.; Stillwell, R.N.; Horning, E.C.; Anal. Chem. 47, 1956-1959, 1975.

[37] Valadbeigi, Y.; Ilbeigi, V.; Michalczuk, B.; Sabo, M.; Matejcik, S.; J. Phys. Chem. A 123, 313-322, 2018.

[38] Grützmacher, H.F.; Caltapanides, A.; J. Am. Soc. Spectrom. 5, 826–836, 1994.

[39] Buda, V.; Andor, M.; Ledeti, A.; Ledeti, I.; Vlase, G.; Vlase, T.; Cristescu, C.; Voicu, M.; Suciu, L.; Tomescu, M.;  Int. J. Mol. Sci. 18, 164-179, 2017.

[40] Ewing, R.G.; Eiceman, G.A.; Harden, C.S.; & Stone, J.A.; Int. J. Mass Spectrom. 255, 76-85, 2006.

[41] Valadbeigi, Y.; Ilbeigi, V.; Mirsharifi, M.S.; J. Mass Spectrom. 55(10), e4586, 2020.

[42] An, X.; Eiceman, G.A.; Räsänen, R.M.; Rodriguez, J.E.; Stone, J. A.; J. Phys. Chem. A 117, 6389-6401, 2013.