Synthesis of a cyclopentane amide DNA analogue and its base pairing properties.
cpa-DNA monomers containing the bases adenine and thymine have been synthesized starting from the known compound 1 in 12 steps. Partially and fully modified cpa-thymidine and cpa-adenosine containing oligodeoxynucleotides were synthesized by standard oligonucleotide chemistry. Fully modified homo-cpa-A sequences lead to duplex destabilization by -1.4 degrees C/mod. relative to DNA. As its congener bca-DNA, cpa-DNA prefers left-handed duplex formation where possible.
Ahn
Dae-Ro
DR
Department of Chemistry and Biochemistry, University of Bern, Bern, Switzerland.
Mosimann
Markus
M
Leumann
Christian J
CJ
D000225:Adenine; D000577:Amides; D020029:Base Pairing; D001483:Base Sequence; D002942:Circular Dichroism; D003517:Cyclopentanes; D004247:DNA / Q000737:chemistry*; D007202:Indicators and Reagents; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013941:Thymine
D000577:Amides; D003517:Cyclopentanes; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D004247:DNA; D000225:Adenine; D013941:Thymine