Base-pairing systems related to TNA: alpha-threofuranosyl oligonucleotides containing phosphoramidate linkages

Xiaolin Wu; Sreenivasulu Guntha; Mathias Ferencic; Ramanarayanan Krishnamurthy; Albert Eschenmoser

doi:10.1021/ol020015x

Base-pairing systems related to TNA: alpha-threofuranosyl oligonucleotides containing phosphoramidate linkages

Org Lett. 2002 Apr 18;4(8):1279-82. doi: 10.1021/ol020015x.

Authors

Xiaolin Wu¹, Sreenivasulu Guntha, Mathias Ferencic, Ramanarayanan Krishnamurthy, Albert Eschenmoser

Affiliation

¹ The Skaggs Institute for Chemical Biology at the Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

PMID: 11950342
DOI: 10.1021/ol020015x

Abstract

(3'NH)- and (2'NH)-TNA, two isomeric phosphoramidate analogues of TNA (alpha-threofuranosyl-(3'-->2') oligonucleotides), are shown to be efficient Watson-Crick base-pairing systems and to undergo intersystem cross-pairing with TNA, RNA, and DNA. [reaction: see text]

Publication types

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

MeSH terms

Amides / chemistry
Base Pairing*
Chromatography, High Pressure Liquid
Circular Dichroism
DNA / chemistry
Furans / chemistry
Indicators and Reagents
Oligonucleotides / chemistry
Phosphoric Acids / chemistry
RNA / chemistry
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Spectrophotometry, Ultraviolet

Substances

Amides
Furans
Indicators and Reagents
Oligonucleotides
Phosphoric Acids
RNA
DNA
phosphoramidic acid