title: Theoretical calculations, synthesis and base pairing properties of oligonucleotides containing 8-amino-2'-deoxyadenosine.
abstract: Theoretical calculations on double and triple helices containing 8-amino-2'-deoxyadenosine were made to analyze the possible differences in base pairing properties between 8-aminoadenine and adenine. These calculations indicate a strong preferential stabilization of the triplex over the duplex when adenine is replaced by 8-aminoadenine. In addition, a protected phosphoramidite derivative of 8-amino-2'-deoxyadenosine was prepared for the introduction of 8-aminoadenine into synthetic oligonucleotides using the phosphite-triester approach. DNA triple helical structures are normally observed at acidic pH. However, when oligonucleotides carrying 8-aminoadenine are used, very stable triple helical structures can be observed even at neutral pH. Biological applications of triple helices could benefit from the use of 8-aminoadenine derivatives.
authors: European Molecular Biology Laboratory, Meyerhofstrasse 1, D-69117 Heidelberg, Germany.
authors: R G
authors: RG
authors: García
authors: E
authors: E
authors: Ferrer
authors: M J
authors: MJ
authors: Macías
authors: R
authors: R
authors: Eritja
authors: M
authors: M
authors: Orozco
mesh_terms: D002851:Chromatography, High Pressure Liquid; D017931:DNA Primers; D003839:Deoxyadenosines / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D013816:Thermodynamics
chemical_list: D017931:DNA Primers; D003839:Deoxyadenosines; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C090166:8-amino-2'-deoxyadenosine