Synthesis and Base Pairing Properties of 1′,5′-Anhydro-L-Hexitol Nucleic Acids (L-HNA)

被引：26

作者：

D'Alonzo, Daniele ^{[2
]}

Van Aerschot, Arthur ^{[1
]}

Guaragna, Annalisa ^{[2
]}

Palumbo, Giovanni ^{[2
]}

Schepers, Guy ^{[1
]}

Capone, Stefania ^{[2
]}

Rozenski, Jef ^{[1
]}

Herdewijn, Piet ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

[2] Univ Naples Federico 2, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 39期

关键词：

DNA analogues; domino reactions; HNA; nucleic acids; oligonucleotides; ANTISENSE OLIGONUCLEOTIDES; HOMO-DNA; BUILDING-BLOCKS; L-NUCLEOSIDES; RNASE-H; L-LNA; HYBRIDIZATION; RECOGNITION; STABILITY; OLIGORIBONUCLEOTIDES;

D O I：

10.1002/chem.200901847

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：10121 / 10131

页数：11