Inclusion complexes of V-amylose with Undecanoic acid (cas 112-37-8) and dodecanol at atomic resolution: X-ray structures with cycloamylose containing 26 d-glucoses (cyclohexaicosaose) as host
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Add time:08/23/2019 Source:sciencedirect.com
Crystal structures are reported of cycloamylose containing 26 d-glucose residues (CA26, cyclohexaicosaose, C156H260O130) in complexes with Undecanoic acid (cas 112-37-8) (CA26·2C10H21COOH·34.95H2O, orthorhombic P212121, one CA26 and two bound undecanoic acids F1 and F2 in the asymmetric unit, resolution 0.95 Å) and with dodecanol ((CA26)0.5·C12H25OH·32.0H2O, monoclinic C2, half a CA26 binding one dodecanol, A, in the asymmetric unit, resolution 1.0 Å). The macrocycle of CA26 is folded like the figure `8' into two 10 d-glucoses long left-handed V-amylose helices forming ∼5 Å wide V-channels that are occupied by undecanoic acid (F1, F2) or dodecanol (A) as guest molecules. The functional head groups of the guests near the O(6) ends of the V-channels are hydrogen bonded with d-glucose O(6)n–H; the aliphatic termini beyond C(9) protrude from the O(2), O(3) ends. Parts of the aliphatic chains enclosed in the V-channels are all-trans except for one torsion angle each (∼130°) in undecanoic acid molecules F1 and F2. There are several (guest)C–H⋯O hydrogen bonds to O(4) and O(6) of CA26 in both complexes, and H⋯H van der Waals interactions with d-glucose C(3)–H and C(5)–H dominate. C(5)–H determine the position of the aliphatic chains of undecanoic acid F1 and of dodecanol A in contrast to F2 where both C(3)–H and C(5)–H contribute equally, probably because the V-channel is narrower than in F1 and in dodecanol. Complexes of polymeric V-amylose with fatty acids and alcohols studied by X-ray fiber diffraction could not provide the here described high resolution.
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