Synthesis and biophysical studies of N2'-functionalized 2'-amino-alpha-L-LNA

T Santhosh Kumar; Andreas S Madsen; Jesper Wengel; Patrick J Hrdlicka

doi:10.1080/15257770701538841

Synthesis and biophysical studies of N2'-functionalized 2'-amino-alpha-L-LNA

Nucleosides Nucleotides Nucleic Acids. 2007;26(10-12):1403-5. doi: 10.1080/15257770701538841.

Authors

T Santhosh Kumar¹, Andreas S Madsen, Jesper Wengel, Patrick J Hrdlicka

Affiliation

¹ Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark. skt@chem.sdu.dk

PMID: 18066792
DOI: 10.1080/15257770701538841

Abstract

A synthetic route towards a selected set of N-acylated and N-alkylated derivatives of 2'-amino-alpha-L-LNA phosphoramidite building blocks has been developed. Biophysical studies suggest that the 2-oxo-5-azabicyclo[2.2.1]heptane skeleton of 2'-amino-alpha-L-LNA allows precise positioning of intercalators in the core of nucleic acid duplexes.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biophysical Phenomena
Biophysics
Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Organophosphorus Compounds / chemistry*
Thymidine Monophosphate / analogs & derivatives*
Thymidine Monophosphate / chemical synthesis
Thymidine Monophosphate / chemistry

Substances

2'-N-(pyren-1-yl)acetyl-2'-amino-alpha-L-LNA
2-oxo-5-azabicyclo(2.2.1)heptane
Bridged Bicyclo Compounds, Heterocyclic
Organophosphorus Compounds
phosphoramidite
Thymidine Monophosphate