Furanosic forms of sugars: conformational equilibrium of methyl β--ribofuranoside

The investigation of an isolated ribofuranose unit in the gas phase reveals the intrinsic conformational landscape of the biologically active sugar form. We report the rotational spectra of two conformers of methyl β- d -ribofuranoside in a supersonic jet expansion. Both conformers adopt a near twis...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-04, Vol.52 (37), p.6241-6244
Main Authors: Écija, Patricia, Uriarte, Iciar, Spada, Lorenzo, Davis, Benjamin G, Caminati, Walther, Basterretxea, Francisco J, Lesarri, Alberto, Cocinero, Emilio J
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Summary:The investigation of an isolated ribofuranose unit in the gas phase reveals the intrinsic conformational landscape of the biologically active sugar form. We report the rotational spectra of two conformers of methyl β- d -ribofuranoside in a supersonic jet expansion. Both conformers adopt a near twisted ( 3 T 2 ) ring conformation with the methoxy and hydroxymethyl substituents involved in various intramolecular hydrogen bonds. The rotational spectrum of the isolated ribofuranoside unit, the biologically active sugar form, revealed two structures with a similar puckering to the RNA units in crystals.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc01180b