title: The readout of base-pair information in adenine-thymine α-D-Arabinonucleosides.
abstract: Structurally modified nucleosides are central players in the field of nucleic acid chemistry. Adenine-thymine (AT) pyrimido[4,5-d]pyrimidine furanosyl and pyranosyl arabinonucleosides have been synthesized for the first time. Single-crystal X-ray diffraction analysis reveals novel base pairs that, in synergy with the sugar residues, direct the emergence of distinct networks containing channels and cavities. The microscopic noncovalent connections can be translated into macroscopic levels in which robust organogels are formed by the furanoside but not the pyranoside. The influences of the sugars are also displayed by the different shaped superstructures of the free nucleosides in solution. The readout of the information in the base moiety is therefore tailored by the sugar configuration, and the interplays exert subtle effects on the structures, from solid to gel and to the solution state. The potential for forming these appealing base pairs and higher structures enables these intriguing nucleosides to serve as unique building blocks in various areas or to construct innovative nucleic acid structures.
authors.affiliation: Institute for Nanobiomedical Technology and Membrane Biology, Regenerative Medicine Research Center, West China Hospital, West China Medical School, Sichuan University, No. 1, Keyuan 4th Road, Gaopengdadao, Chengdu 610041 (China).
authors.forename: Shiliang
authors.initials: S
authors.lastname: He
authors.forename: Hang
authors.initials: H
authors.lastname: Zhao
authors.forename: Xiurong
authors.initials: X
authors.lastname: Guo
authors.forename: Xiaoping
authors.initials: X
authors.lastname: Xu
authors.forename: Xinglong
authors.initials: X
authors.lastname: Zhou
authors.forename: Jiang
authors.initials: J
authors.lastname: Liu
authors.forename: Zhihua
authors.initials: Z
authors.lastname: Xing
authors.forename: Ling
authors.initials: L
authors.lastname: Ye
authors.forename: Lu
authors.initials: L
authors.lastname: Jiang
authors.forename: Qianming
authors.initials: Q
authors.lastname: Chen
authors.forename: Yang
authors.initials: Y
authors.lastname: He
mesh_terms: D000225:Adenine / Q000737:chemistry* / Q000378:metabolism; D001087:Arabinonucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D020029:Base Pairing; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D013941:Thymine / Q000737:chemistry*
chemical_list: D001087:Arabinonucleosides; D000225:Adenine; D013941:Thymine
keywords: base pairs; nucleosides; self-assembly; supramolecular chemistry