LNA 5'-phosphoramidites for 5'→3'-oligonucleotide synthesis

Andreas Stahl Madsen; T Santhosh Kumar; Jesper Wengel

doi:10.1039/c0ob00346h

LNA 5'-phosphoramidites for 5'→3'-oligonucleotide synthesis

Org Biomol Chem. 2010 Nov 7;8(21):5012-6. doi: 10.1039/c0ob00346h. Epub 2010 Sep 3.

Authors

Andreas Stahl Madsen¹, T Santhosh Kumar, Jesper Wengel

Affiliation

¹ Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230, Odense M, Denmark. [email protected]

PMID: 20820663
DOI: 10.1039/c0ob00346h

Abstract

Hereby we report an efficient synthesis of LNA thymine and LNA 5-methylcytosine 5'-phosphoramidites, allowing incorporation of LNA thymine and LNA 5-methylcytosine into oligonucleotides synthesized in the 5'→3' direction. Key steps include regioselective enzymatic benzoylation of the 5'-hydroxy group of unprotected LNA thymine, and subsequent 4,4'-dimethoxytritylation of the 3'-hydroxy group of the O5'-benzoylated LNA thymine nucleoside.

Publication types

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

MeSH terms

5-Methylcytosine / chemistry*
5-Methylcytosine / metabolism
Candida / enzymology
Fungal Proteins
Lipase / metabolism
Molecular Structure
Oligonucleotides / chemistry*
Oligonucleotides / metabolism
Organophosphorus Compounds / chemistry*
Organophosphorus Compounds / metabolism
Stereoisomerism
Thymine / chemistry*
Thymine / metabolism

Substances

Fungal Proteins
Oligonucleotides
Organophosphorus Compounds
phosphoramidite
5-Methylcytosine
Lipase
lipase B, Candida antarctica
Thymine