Synthesis and incorporation into DNA of a chemically stable, functional abasic site analogue.
[reaction: see text] The abasic site building block 7 for DNA synthesis, containing a methylenephosphinic acid group at C3', was prepared in six steps and was incorporated into DNA via a combination of H-phosphonate and phosphoramidite chemistry. Corresponding oligodeoxynucleotides were shown to be chemically stable under basic conditions and fully functional at the respective hemiacetal center.
Mosimann
Markus
M
Department of Chemistry & Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Küpfer
Pascal A
PA
Leumann
Christian J
CJ
D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry*; D004260:DNA Repair; D007202:Indicators and Reagents; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D010720:Phosphines / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D010720:Phosphines; D004247:DNA