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

The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies
The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies
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).
crystal structure, fluorinated carbohydrate, pyranose, chair conformation, anomer, nmr
0008-6215
1129-1139
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Golten, Samuel
214a0aed-950c-41b0-8b3f-b71614ce9d5e
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Sebban, Muriel
dc6835fb-12d0-4a1a-a7d2-dd13d5045300
Oulyadi, Hassan
fa78fc84-2806-4a25-8675-3194c3d7a2ce
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Golten, Samuel
214a0aed-950c-41b0-8b3f-b71614ce9d5e
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Sebban, Muriel
dc6835fb-12d0-4a1a-a7d2-dd13d5045300
Oulyadi, Hassan
fa78fc84-2806-4a25-8675-3194c3d7a2ce

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), 1129-1139. (doi:10.1016/j.carres.2011.04.007). (PMID:21531398)

Record type: Article

Abstract

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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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: 15 Mar 2024 03:05

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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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