title: Bifacial nucleoside as a surrogate for both T and A in duplex DNA.
abstract: A new functional bifacial nucleoside derived from 7-aminopyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione, a Janus-type nucleobase, has been synthesized and incorporated into DNA oligonucleotides. The nucleobase, having self-complementary H-bonding faces, mimics both T and A and engages in the corresponding Watson-Crick-like base pairs, forming stable duplexes.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0358, USA.
authors.forename: Dongwon
authors.initials: D
authors.lastname: Shin
authors.forename: Yitzhak
authors.initials: Y
authors.lastname: Tor
mesh_terms: D000241:Adenosine / Q000737:chemistry*; D020029:Base Pairing; D004247:DNA / Q000737:chemistry*; D006860:Hydrogen Bonding; D018716:Molecular Mimicry; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D011744:Pyrimidinones / Q000737:chemistry*; D013816:Thermodynamics; D013936:Thymidine / Q000737:chemistry*
chemical_list: C560522:7-aminopyrimido(4,5-d)pyrimidine-2,4(1H,3H)-dione; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D011744:Pyrimidinones; D004247:DNA; D000241:Adenosine; D013936:Thymidine