title: Construction of a self-complementary nucleoside from deoxyguanosine.
abstract: The 8-hydroxyguanine:adenine mispairing scheme that spontaneously occurs in vivo through oxidative metabolism of DNA was edited to obtain a pair closely fitting the Watson-Crick geometry in which 2 purine bases of identical structure but oppositely rotated in the syn and anti configurations are hydrogen-bonded. The structure thus designed, 2-amino-8-hydroxypurine, was synthesized as a DNA precursor from deoxyguanosine in 8 steps by oxidation at carbon 8 of guanine followed by reduction at carbon 6. Polydeoxynucleotides embodying this self-complementary base are expected to undergo direct copying processes through polymerase catalysis.
authors.affiliation: Unité de chimie organique, Institut Pasteur, Paris, France.
authors.forename: S
authors.initials: S
authors.lastname: Pochet
authors.forename: P
authors.initials: P
authors.lastname: Marlière
mesh_terms: D001482:Base Composition; D001483:Base Sequence; D004261:DNA Replication; D018076:DNA, Complementary / Q000138:chemical synthesis*; D003849:Deoxyguanosine / Q000378:metabolism*; D006147:Guanine / Q000031:analogs & derivatives; D008969:Molecular Sequence Data; D009690:Nucleic Acid Conformation
chemical_list: D018076:DNA, Complementary; D006147:Guanine; D003849:Deoxyguanosine