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Constrained Nucleoside Analogues – Crystal And Molecular Structure Of 6,5′-O-anhydrouridines Fixed In The Anti Conformation

R. Gajda, M. Baginski, M. Baginski, Ewelina Tomczyk, Ewelina Tomczyk, Adam Mieczkowski, K. Woźniak
Published 2015 · Chemistry

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Abstract A series of analogues of anhydrouridine have been synthesized and their crystal structures established using X-ray diffraction. For all cases, the ribose ring has O(4′)-exo, C(4′)-endo pucker and the pyrimidine base is in the anti conformation. Investigated compounds crystallize in different crystal systems (monoclinic, orthorhombic), have different space group symmetry ( P 2 1 , P 2 1 2 1 2 1 ) and exhibit different intermolecular interactions (halogen and hydrogen bonds) among molecules in their crystal lattices. Moreover, in the case of the 5-benzyl-6,5′- O -anhydrouridine a significant positional disorder is present with the phenyl rings existing in two orientations.
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