Small molecules NMR: Carbohydrates
The “classical” challenge, raised by Emil Fischer as to why one monosaccharide arylhydrazone adopts a cyclic structure but another an acyclic structure, is answered here. The present comprehensive analysis of hexose and hexosamine arylhydrazones, based on 2D NMR spectroscopy and theoretical modeling, has established that the chain of hydrogen bonds needed for conformational selection can only be completed for D-glucosamine derivatives.
Classical 1D, 2D homo- and heteronculear NMR (1H, 13C, 15N,19F, 31P) approaches are used for molecular assignment, reaction mechanism elucidation in a temperature range of -50 °C ̶ +45 °C for different types of small molecules and short peptides.
Related publications
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Viktória Goldschmidt Gőz , István Pintér , Antal Csámpai , Imre Jákli , Virág Zsoldos-Mády , András Perczel
Hydrogen-Bonding Network Anchors the Cyclic Form of Sugar Arylhydrazones
Eur. J. Org. Chem. 20:3419-3426. DOI: 10.1002/ejoc.201600462 (2016) Kivonat