2D-IR spectroscopy of carbohydrates: Characterization of thiocyanate-labeled β-glucose in CHCl3 and H2O

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Abstract
Carbohydrates constitute one of the four key classes of biomacromolecules but have not been studied by 2D-IR spectroscopy so far. Similarly as for proteins, their chemical structure and the repetitive nature of native vibrational oscillators, combined with their huge structural diversity, lead to spectrally congested infrared spectra already for singlecarbohydrates. Biophysical studies are further impeded by the strong overlap between water modes and carbohydrates modes. Here, we demonstrate the application of the known vibrational reporter group thiocyanate (SCN) in glucose. In his first study, we are able to perform IR- and 2D-IR spectroscopy of β -glucose with SCN at C2 position, as proof of concept in chloroform. Upon improved synthesis and removal of all protecting groups we succeed to perform 2D-IR in H2O. All experiments are compared to results of methyl-thiocyanate as reference sample. Overall we show that theconcept of using site-specific vibrational reporter groups can be transferred to carbohydrates.
Funding Information
  • Deutsche Forschungsgemeinschaft (EXC 2008/1 - 390540038)
  • EFRE-InfraFEI Brandenburg (85045645)
  • EFRE-StaF Brandenburg (85037875)

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