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| - Crystal Structure of a B-Form DNA Duplex Containing(l)-α-Threofuranosyl (3‘→2‘) Nucleosides: A Four-CarbonSugar Is Easily Accommodated into the Backbone of DNA
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| - (l)-α-Threofuranosyl-(3‘→2‘)-oligonucleotides (TNA) containing vicinally connected phosphodiester linkages undergo informational base pairing in an antiparallel strand orientation and are capable ofcross-pairing with RNA and DNA. TNA is derived from a sugar containing only four carbon atoms and isone of the simplest potentially natural nucleic acid alternatives investigated thus far in the context of achemical etiology of nucleic acid structure. Compared to DNA and RNA that contain six covalent bondsper repeating nucleotide unit, TNA contains only five. We have determined the atomic-resolution crystalstructure of the B-form DNA duplex [d(CGCGAA)T*d(TCGCG)]2 containing a single (l)-α-threofuranosylthymine (T*) per strand. In the modified duplex base stacking interactions are practically unchanged relativeto the reference DNA structure. The orientations of the backbone at the TNA incorporation sites are slightlyaltered in order to accommodate fewer atoms and covalent bonds. The conformation of the threose isC4‘-exo with the 2‘- and 3‘-substituents assuming quasi-diaxial orientation.
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