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Sweet Structural Signatures Unveiled in Ketohexoses
Author(s) -
Bermúdez Celina,
Peña Isabel,
Mata Santiago,
Alonso José L.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603223
Subject(s) - conformational isomerism , rotational spectroscopy , intramolecular force , chemistry , hydrogen bond , fourier transform , spectroscopy , molecule , crystallography , stereochemistry , physics , mathematics , organic chemistry , mathematical analysis , quantum mechanics
Abstract The conformational behaviour of naturally occurring ketohexoses has been revealed in a supersonic expansion by Fourier transform microwave spectroscopy coupled with a laser ablation source. Three, two and one conformers of d ‐tagatose, d ‐psicose and l ‐sorbose, respectively, have been identified by their rotational constants extracted from the analysis of the spectra. Singular structural signatures involving the hydroxyl groups OH (1) and OH (2) have been disentangled from the intricate intramolecular hydrogen bond networks stabilising the most abundant conformers. The present results place the old Shallenberger and Kier sweetness theories on a firmer footing.