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Macrocyclic substructure of tricolorin A – The first crystal structure of a resin glycoside

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Lehmann,  Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Müller,  Thomas
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Lehmann, C. W., Fürstner, A., & Müller, T. (2000). Macrocyclic substructure of tricolorin A – The first crystal structure of a resin glycoside. Zeitschrift für Kristallographie: International Journal for Structural, Physical, and Chemical Aspects of Crystalline Materials, 215(2), 114-117. doi:10.1524/zkri.2000.215.2.114.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-2749-B
Abstract
The structure of a tricolorin A derivative (11S)-11-[[4,6-O-benzylidene-β-D-glucopyranosyl-(1 → 2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoic acid 3gluc-lactone 2, a member of the resin glycosides, has been determined. This crystal structure is the first example for this class of natural products. At 100 K the lattice parameters in monoclinic space group P21 are: a=22.502(5)Å, b=17.339(4)Å, c=25.011(5)Å, β=92.49(3)°, V=9749(3)Å3 , Z=10. M=705.67, ρ=1.202 Mg m-3 , μ=0.087 mm-1 , F(000)=3824. The five crystallographically independent molecules show upon superpositioning the expected preservation of the glycosidic link geometry, however the alkyl part of the macrocyclic ring expresses a larger degree of freedom while conserving gauche and anti conformations in six of nine torsion angles.