Investigation of chemical transformations of thiophenylglycoside of muramyl dipeptide on the fumed silica surface using TPD-MS, FTIR spectroscopy and ES IT MS

Liana R Azizova; Tetiana V Kulik; Borys B Palianytsia; Aleksandr E Zemlyakov; Viktoriya N Tsikalova; Vasiliy Ya Chirva

doi:10.1186/1556-276X-9-234

Investigation of chemical transformations of thiophenylglycoside of muramyl dipeptide on the fumed silica surface using TPD-MS, FTIR spectroscopy and ES IT MS

Nanoscale Res Lett. 2014 May 13;9(1):234. doi: 10.1186/1556-276X-9-234. eCollection 2014.

Authors

Liana R Azizova¹, Tetiana V Kulik¹, Borys B Palianytsia¹, Aleksandr E Zemlyakov², Viktoriya N Tsikalova², Vasiliy Ya Chirva²

Affiliations

¹ Chuiko Institute of Surface Chemistry, The National Academy of Sciences of Ukraine, 17 Generala Naumova Str., 17, Kyiv 03164, Ukraine.
² Taurida National V.I. Vernadsky University, Akademika Vernadskogo av. 4, Simferopol 95007, Ukraine.

Abstract

In this study, chemical transformations of benzyl ester of О-(phenyl-2-acetamido-2,3-dideoxy-1-thio-β-d-glucopyranoside-3-yl)-d-lactoyl-l-alanyl-d-isoglutamine (SPhMDPOBn) on the fumed silica surface were examined, and the surface complex structure was characterized by temperature-programmed desorption mass spectrometry (TPD-MS), infrared spectroscopy (FTIR) and electrospray ion trap mass spectrometry (ES IT MS). Stages of pyrolysis of SPhMDPOBn in pristine state and on the silica surface have been determined. Probably, hydrogen-bonded complex forms between silanol surface groups and the C = O group of the acetamide moiety NH-(CH3)-C = O…H-O-Si≡. The thermal transformations of such hydrogen-bonded complex result in pyrolysis of SPhMDPOBn immobilized on the silica surface under TPD-MS conditions. The shifts ∆ν of amide I band (measured from 1,626 to 1,639 cm(-l) for SPhMDPOBn in pristine state) of 33 and 35 cm(-l) which occurred when SPhMDPOBn was immobilized on the silica surface may be caused by a weakening of the intramolecular hydrogen bonding of the SPhMDPOBn because the interaction with the silica surface as hydrogen bond with silanol groups is weaker than that in associates.

Keywords: Electrospray ion trap mass spectrometry (ESI IT MS); Fourier transform infrared spectroscopy (FTIR); Muramyl dipeptide; Pyrolysis; Temperature-programmed desorption mass spectrometry (TPD-MS); Thioglycosides.