Phenylalkyl backbone modified oligodeoxynucleotides, their synthesis and the influence of the alkyl chain length.
Phenylalkyl modified phosphoramidites (alkyl chain length n = 1, 2, 3, 5; Fig. 1) were synthesised and incorporated into a DNA hexamer (5'-d(GCCp-GCG); p = place of modification). The obtained diastereomeres were separated by RP-HPLC. After hybridisation with the complementary DNA strand Tm-value and thermodynamic data were measured. The stability of duplexes depends on the linker length and the absolute configuration of the backbone modified oligodeoxynucleotides (Rp, Sp).
Amberg
S
S
Institut für Organische Chemie, Johann Wolfgang Goethe-Universität, Marie Curie Strasse 11, D-60439 Frankfurt am Main, Germany.
Engels
J W
JW
D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013329:Structure-Activity Relationship
D006841:Hydrocarbons, Aromatic; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite