Methyl 3-O-α-l-fucopyranosyl α-d-gal­acto­pyran­oside: a synchrotron study

Eriksson, L.; Widmalm, G.

doi:10.1107/S1600536812002279

Volume 68
Part 2
Page o528
February 2012

Received 15 December 2011
Accepted 18 January 2012
Online 31 January 2012

Key indicators
Single-crystal Synchrotron study
T = 100 K
Mean (C-C) = 0.009 Å
R = 0.060
wR = 0.177
Data-to-parameter ratio = 5.4
Details

Methyl 3-O--L-fucopyranosyl -D-galactopyranoside: a synchrotron study

Lars Eriksson ^a ^* and Göran Widmalm ^b

^aDepartment of Material and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden, and ^bDepartment of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden
Correspondence e-mail: lars.eriksson@mmk.su.se

The title compound, C₁₃H₂₄O₁₀ is the methyl glycoside of a structural element [alpha] -L-Fucp-(1 [rightwards arrow] 3)- [alpha] -D-Galp making up two thirds of the repeating unit in the capsular polysaccharide of Klebsiella K63. The conformation of the title compound is described by the glycosidic torsion angles [varphi] _H = 55 (1)° and [psi] _H = -24 (1)°. The hydroxymethyl group in the galactose residue is present in the gauche-trans conformation. In the crystal, O-HO hydrogen bonds connect the disaccharide units into chains along the a-axis direction and further hydrogen bonds cross-link the chains.

Related literature

The capsular polysaccharide (CPS) of Klebsiella K63 contains a repeating unit consisting of [rightwards arrow] 3)- [alpha] -D-GalpA-(1 3)- [alpha] -L-Fucp-(1 3)- [alpha] -D-Galp-(1 , see: Joseleau & Marais (1979). For an investigation of the CPS S-156 from Klebsiella pneumoniae ATCC 316 46, see: Johansson et al. (1994) and of the CPS from Klebsiella pneumoniae I-1507, see: Guetta et al. (2003). For a fiber X-ray diffraction study of the Klebsiella K63 CPS, see: Elloway et al. (1980 $[Elloway, H. F., Isaac, D. H. & Atkins, E. T. D. (1980). Fiber Diffraction Methods, ACS Symposium Series, 141, 429-458.]$ ). For the synthesis, see: Baumann et al. (1988).

Experimental

Crystal data

C₁₃H₂₄O₁₀
M_r = 340.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.78478 (11) Å
b = 15.7859 (5) Å
c = 19.4401 (5) Å
V = 1468.36 (7) Å³
Z = 4
Synchrotron radiation
= 0.907 Å
= 0.13 mm^-1
T = 100 K
0.03 × 0.01 × 0.01 mm

Data collection

Marresearch MARCCD 165 diffractometer
7469 measured reflections
1162 independent reflections
975 reflections with I > 2(I)
R_int = 0.117
_max = 30.1°

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.177
S = 1.09
1162 reflections
216 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3f-H3f1O6gⁱ	0.84	1.93	2.772 (7)	177
O4f-H4f1O3fⁱⁱ	0.84	2.04	2.880 (7)	175
O2g-H2g1O2gⁱⁱⁱ	0.84	1.92	2.680 (7)	149
O4g-H4g1O5f^iv	0.84	2.08	2.827 (6)	149
O6g-H6gO3f^v	0.84	2.02	2.822 (7)	158
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) x+1, y, z; (v) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: MARCCD (Marresearch, 2010); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6569 ).

Acknowledgements

This work was supported by a grant from the Swedish Research Council and by the Faculty of Natural Sciences at Stockholm University

References

Baumann, H., Jansson, P.-E. & Kenne, L. (1988). J. Chem. Soc. Perkin Trans. 1, pp. 209-217.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Elloway, H. F., Isaac, D. H. & Atkins, E. T. D. (1980). Fiber Diffraction Methods, ACS Symposium Series, 141, 429-458.
Guetta, O., Mazeau, K., Auzely, R., Milas, M. & Rinaudo, M. (2003). Biomacromolecules, 4, 1362-1371.
Johansson, A., Jansson, P.-E. & Widmalm, G. (1994). Carbohydr. Res. 253, 317-322.
Joseleau, J.-P. & Marais, M.-R. (1979). Carbohydr. Res. 77, 183-190.
Marresearch (2010). MARCCD. Marresearch GmbH, Norderstedt, Germany.
Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds