title: Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine.
abstract: The synthesis of a diaminopurine PNA monomer, N-[N6-(benzyloxycarbonyl)-2,6-diaminopurine-9-yl] acetyl-N-(2-t-butyloxycarbonylaminoethyl)glycine, and the incorporation of this monomer into PNA oligomers are described. Substitution of adenine by diaminopurine in PNA oligomers increased the T m of duplexes formed with complementary DNA, RNA or PNA by 2.5-6.5 degrees C per diaminopurine. Furthermore, discrimination against mismatches facing the diaminopurine in the hybridizing oligomer is improved. Finally, a homopurine decamer PNA containing six diaminopurines is shown to form a (gel shift) stable strand displacement complex with a target in a 246 bp double-stranded DNA fragment.
authors.affiliation: Center for Biomolecular Recognition, Department of Chemistry, The H. C.Orsted Institute, Universitetsparken 5, DK-2100 Copenhagen O, Denmark.
authors.forename: G
authors.initials: G
authors.lastname: Haaima
authors.forename: H F
authors.initials: HF
authors.lastname: Hansen
authors.forename: L
authors.initials: L
authors.lastname: Christensen
authors.forename: O
authors.initials: O
authors.lastname: Dahl
authors.forename: P E
authors.initials: PE
authors.lastname: Nielsen
mesh_terms: D015075:2-Aminopurine / Q000031:analogs & derivatives* / Q000378:metabolism; D000225:Adenine; D004247:DNA / Q000378:metabolism*; D018716:Molecular Mimicry; D009696:Nucleic Acids / Q000138:chemical synthesis / Q000378:metabolism*; D009757:Nylons / Q000138:chemical synthesis / Q000378:metabolism*; D010455:Peptides / Q000737:chemistry
chemical_list: D009696:Nucleic Acids; D009757:Nylons; D010455:Peptides; D015075:2-Aminopurine; C007300:2,6-diaminopurine; D004247:DNA; D000225:Adenine