title: Hydrogen-bonding linkage of thymidine derivatives with carboxylic acid and pyridyl groups in a crystalline state.
abstract: Thymidine derivatives with carboxylic acid and pyridyl groups were synthesized for constructing one-dimensional network structure based on hydrogen bonding in crystalline state. The solid sate structures and hydrogen bonding networks of the thymidine derivatives were characterized by single X-ray diffraction analysis. The thymidine derivatives formed a zwitterion structure with a pyridinium proton and a carboxylate moiety in a crystalline state due to transfer of a proton from the carboxylic acid to the pyridyl moiety. Strong hydrogen bonds between the pyridinium proton and the carboxylate moiety connected the thymidine units, resulting in a one-dimensional polymeric structure with a uniform direction reminiscent of the structure of single-strand polythymidine. The chemical structure of the pyridyl group affects the hydrogen-bonding networks. The well-designed hydrogen-bonding interaction served as connecting parts for polythymidine mimics even in the presence of other hydrogen-bonding motifs such as nucleobases.
authors.affiliation: Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Japan.
authors.forename: Junichi
authors.initials: J
authors.lastname: Hoshino
authors.forename: Junpei
authors.initials: J
authors.lastname: Kuwabara
authors.forename: Takaki
authors.initials: T
authors.lastname: Kanbara
mesh_terms: D003460:Crystallization / Q000379:methods*; D006860:Hydrogen Bonding; D046911:Macromolecular Substances / Q000737:chemistry; D008422:Materials Testing; D008968:Molecular Conformation; D049329:Nanostructures / Q000737:chemistry* / Q000648:ultrastructure*; D010316:Particle Size; D011725:Pyridines / Q000737:chemistry*; D013499:Surface Properties; D013936:Thymidine / Q000138:chemical synthesis*
chemical_list: D046911:Macromolecular Substances; D011725:Pyridines; C023666:pyridine; D013936:Thymidine