NDLI: Co-crystals of 3-deoxy-3-fluoro-α-D-glucopyranose and 3-deoxy-3-fluoro-β-D-glucopyranose.

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Co-crystals of 3-deoxy-3-fluoro-α-D-glucopyranose and 3-deoxy-3-fluoro-β-D-glucopyranose.

Content Provider	Europe PMC
Author	Zhang, Wenhui Oliver, Allen G. Serianni, Anthony S.
Copyright Year	2010
Abstract	3-Deoxy-3-fluoro-d-glucopyranose crystallizes from acetone to give a unit cell containing two crystallographically independent molecules. One of these molecules (at site A) is structurally homogeneous and corresponds to 3-deoxy-3-fluoro-β-d-glucopyranose, C6H11FO5, (I). The second molecule (at site B) is structurally heterogeneous and corresponds to a mixture of (I) and 3-deoxy-3-fluoro-α-d-glucopyranose, (II); treatment of the diffraction data using partial-occupancy oxygen at the anomeric center gave a high-quality packing model with an occupancy ratio of 0.84:0.16 for (II):(I) at site B. The mixture of α- and β-anomers at site B appears to be accommodated in the lattice because hydrogen-bonding partners are present to hydrogen bond to the anomeric OH group in either an axial or equatorial orientation. Cremer–Pople analysis of (I) and (II) shows the pyranosyl ring of (II) to be slightly more distorted than that of (I) [θ(I) = 3.85 (15)° and θ(II) = 6.35 (16)°], but the general direction of distortion is similar in both structures [ϕ(I) = 67 (2)° (B C1,C4) and ϕ(II) = 26.0 (15)° (C3 TB C1); B = boat conformation and TB = twist-boat conformation]. The exocyclic hydroxymethyl (–CH2OH) conformation is gg (gauche–gauche) (H5 anti to O6) in both (I) and (II). Structural comparisons of (I) and (II) to related unsubstituted, deoxy and fluorine-substituted monosaccharides show that the gluco ring can assume a wide range of distorted chair structures in the crystalline state depending on ring substitution patterns.
Related Links	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC3089378&blobtype=pdf
ISSN	01082701
Volume Number	66
PubMed Central reference number	PMC3089378
Issue Number	Pt 11
Issue Number	pt 11
PubMed reference number	21051824
Journal	Acta Crystallographica Section C: Crystal Structure Communications [Acta Crystallogr C]
e-ISSN	16005759
DOI	10.1107/s0108270110040096
Language	English
Publisher	International Union of Crystallography
Publisher Date	2010-10-21
Access Restriction	Open
Rights License	© International Union of Crystallography 2010
Content Type	Text
Resource Type	Article
Subject	Biochemistry, Genetics and Molecular Biology

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