Synthesis of Glycol Nucleic Acids

Lilu Zhang; Adam E. Peritz; Patrick J. Carroll; Eric Meggers

doi:10.1055/s-2006-926313

PAPER

Synthesis of Glycol Nucleic Acids

Lilu Zhang, Adam E. Peritz, Patrick J. Carroll, Eric Meggers*
Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104, USA
Fax: +1(215)7460348; e-Mail: meggers@sas.upenn.edu;

Abstract

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Abstract

Starting from glycidol, the synthesis of dimethoxytritylated glycol nucleoside phosphoramidites of adenine (A), thymine (T), uracil (U), guanine (G), and cytosine (C) is reported. These phosphoramidites are the building blocks for the automated solid phase synthesis of glycol nucleic acids (GNA) oligonucleotides and it is demonstrated that derived GNA duplexes with completely acyclic backbones considerably exceed the thermal stabilities of analogous DNA duplexes.

Key words

GNA - glycol nucleic acid - glycol nucleotides - acyclic nucleic acid backbone - epoxide ring opening

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References

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