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pubmed-article:19739223pubmed:abstractTextOligonucleotides 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 heterochiral associations were found. Besides T(m) 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 oligonucleotides.lld:pubmed
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pubmed-article:19739223pubmed:articleTitleSynthesis and base pairing properties of 1',5'-anhydro-L-hexitol nucleic acids (L-HNA).lld:pubmed
pubmed-article:19739223pubmed:affiliationDipartimento di Chimica Organica e Biochimica, Università Federico II, Napoli, via Cinthia 4, 80126 Napoli, Italy.lld:pubmed
pubmed-article:19739223pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:19739223pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed