PMID: 3763408Sep 25, 1986Paper

Alkyl phosphotriester modified oligodeoxyribonucleotides. VI. NMR and UV spectroscopic studies of ethyl phosphotriester (Et) modified Rp-Rp and Sp-Sp duplexes, (d[GGAA(Et)TTCC])2

Nucleic Acids Research
M F SummersG Zon

Abstract

1H NMR chemical shift assignments for the title compounds were made for all but a few H5' and H5" signals using two-dimensional nuclear Overhauser effect (2D-NOE) data, which was also used for the first time to assign absolute configuration at phosphorus. The chemical shifts were, in general, similar to those reported [Broido, M.S., et al. (1985) Eur. J. Biochem. 150, 117-128] for the B-like conformation of the unmodified, parent duplex, [d(GGAATTCC)]2. Differences in chemical shifts for corresponding protons were mostly localized to the AA(Et)TT region, and showed some stereochemical dependence. Unambiguous assignment of the phosphotriester 31P signals was achieved in a novel way using selective insensitive nucleus enhancement by polarization transfer (selective INEPT) NMR. The Rp-Rp duplex melted ca. 11 degrees C lower than either the Sp-Sp or parent duplexes, as evidenced by Tm and variable temperature 1H/31P NMR measurements. The 2D-NOE data for the Rp-Rp duplex suggested possible steric interactions between the ethyl group and the H3' of the flanking A residue. At low ionic strength, the Sp-Sp and parent duplexes had similar stability but at high ionic strength the Sp-Sp duplex was less stable.

References

Jun 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·B D StollarR W Pastor
Mar 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·L CallahanK Agarwal
Apr 25, 1986·Nucleic Acids Research·R L LetsingerJ S Eadie
Jan 1, 1982·CRC Critical Reviews in Biochemistry·P Modrich
Jun 29, 1984·Biochemical and Biophysical Research Communications·K LaiD G Gorenstein
Apr 11, 1984·Nucleic Acids Research·S A NobleM H Caruthers

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Citations

Jun 1, 1995·Current Opinion in Structural Biology·A De MesmaekerS Wendeborn
May 1, 1997·Bioorganic & Medicinal Chemistry·H LiB R Shaw
Nov 19, 2009·Mutagenesis·George D D JonesPeter B Farmer
Jun 10, 1988·Nucleic Acids Research·W D WilsonG Zon
Sep 18, 2008·Nucleic Acids Research·Alexandre V LebedevGerald Zon
Dec 1, 1988·European Journal of Biochemistry·F J Van de Ven, C W Hilbers
Oct 31, 2007·Chemical Reviews·Ping LiBarbara Ramsay Shaw

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