Title: Synthesis and Base Pairing Properties of 1 ',5 '-Anhydro-L-Hexitol Nucleic Acids (L-HNA)
Authors: D'Alonzo, Daniele
Van Aerschot, Arthur
Guaragna, Annalisa
Palumbo, Giovanni
Schepers, Guy
Capone, Stefania
Rozenski, Jef
Herdewijn, Piet # ×
Issue Date: 2009
Publisher: VCH Verlagsgesellschaft
Series Title: Chemistry - a European Journal vol:15 issue:39 pages:10121-10131
Abstract: Oligonucleotides composed of 1'-5'-anhydor-arabino-hexitol nucleosides belonging to the L series (L-HNA) were prepared and preliminary studied as a novel potential base-pairing,, system. Synthesis of enantiopureL-hexitol 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 oligonucelotide analogues lucre evaluated in duplex formation with natureal complements as well as with unnatural sugar-modified oligonucelotide. In many cases stable homo- mid hetero-chiral assciations lucre found Besides Tm measurements, detection of heterochiral 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 oligonucelotides.
ISSN: 0947-6539
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Faculty of Pharmaceutical Sciences - miscellaneous
Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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