1. Synthesis and base pairing properties of 1',5'-anhydro-l-hexitol nucleic acids (l-HNA)
- Author
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Stefania Capone, Jef Rozenski, Piet Herdewijn, Arthur Van Aerschot, Giovanni Palumbo, Daniele D'Alonzo, Guy Schepers, Annalisa Guaragna, D'Alonzo, Daniele, A., Van Aerschot, Guaragna, Annalisa, Palumbo, Giovanni, G., Scheper, Capone, Stefania, J., Rozenski, P., Herdeweijn, Van Aerschot, A., Schepers, G., Capone, S., Rozenski, J., and Herdewijn, P.
- Subjects
Models, Molecular ,Circular dichroism ,DNA analogue ,Base pair ,Stereochemistry ,Catalysis ,Cascade reaction ,domino reaction ,Nucleic Acids ,Moiety ,Nucleotide ,Base Pairing ,chemistry.chemical_classification ,Binding Sites ,oligonucleotides ,Base Sequence ,Oligonucleotide ,Chemistry ,Organic Chemistry ,Nucleosides ,Stereoisomerism ,DNA ,General Chemistry ,Arabinose ,nucleic acid ,Enantiopure drug ,HNA ,Nucleic acid ,Nucleic Acid Conformation - Abstract
Oligonucleotides composed of 1',5'-anhydro-arabino-hexitol nucleosides belonging to the L series ( L -HNA) were prepared and preliminarily studied as a novel potential base-pairing system. Synthesis of enantiopure L -hexitol nucleotide monomers equipped with a 2'-(N 6 -benzoyladenin-9-yl) or a 2'-(thymin-1-yl) moiety was carried out by a de novo approach based on a domino reaction as key step. The L oligonucleotide analogues were evaluated in duplex formation with natural complements as well as with unnatural sugar-modified oligonucleotides. In many cases stable homo- and hetero-chiral associations were found. Besides T m measurements, detection of hetero-chiral complexes was unambiguously confirmed by LC-MS studies. Interestingly, circular dichroism measurements of the most stable duplexes suggested that L -HNA form left-handed helices with both D and L oligonucleotides.
- Published
- 2009