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The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies

Record type: Article

The first single-crystal X-ray diffraction study of tetrafluorinated monosaccharide derivatives is presented.
Both a- and b-methyl 2,3-dideoxy-2,2,3,3-tetrafluoro-D-galactopyranoside anomers adopt the
4C1 conformation. The values for the C1–O1 and C1–O5 bond lengths and the O5–C1–O1–CH3 dihedral
angles are in line with what can be expected from the anomeric and exo-anomeric effects. The chair conformations
are slightly distorted, presumably due to repulsion between 1,3-diaxial C–O and C–F bonds.
The asymmetric unit of both compounds contains up to three independent molecules, which differ in
the conformation of the hydroxymethyl group (including in one case a ‘forbidden’ gg rotamer). The
molecular packing of the b-anomer shows a clear segregation between fluorinated and hydrophilic
domains, while for the a-anomer the regions of fluorine segregation are broken by interleafing of OMe
groups. There is one close OH? ? ?F contact, which is likely to arise from the crystal packing. NMR studies
show that the two anomers also adopt a 4C1 conformation in solution (D2O, CDCl3).

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Citation

Linclau, Bruno, Golten, Samuel, Light, Mark, Sebban, Muriel and Oulyadi, Hassan (2011) The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies Carbohydrate Research, 346, (9), pp. 1129-1139. (doi:10.1016/j.carres.2011.04.007). (PMID:21531398).

More information

Published date: 1 July 2011
Keywords: crystal structure, fluorinated carbohydrate, pyranose, chair conformation, anomer, nmr

Identifiers

Local EPrints ID: 185957
URI: http://eprints.soton.ac.uk/id/eprint/185957
ISSN: 0008-6215
PURE UUID: e100ff88-5ee3-4e59-a1ef-d11f8f3f1ed0
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 11 May 2011 13:19
Last modified: 18 Apr 2017 02:15

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Contributors

Author: Bruno Linclau ORCID iD
Author: Samuel Golten
Author: Mark Light ORCID iD
Author: Muriel Sebban
Author: Hassan Oulyadi

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