Literature DB >> 3786144

Phosphorothioate-modified oligodeoxyribonucleotides. III. NMR and UV spectroscopic studies of the Rp-Rp, Sp-Sp, and Rp-Sp duplexes, [d(GGSAATTCC)]2, derived from diastereomeric O-ethyl phosphorothioates.

L A LaPlanche, T L James, C Powell, W D Wilson, B Uznanski, W J Stec, M F Summers, G Zon.   

Abstract

2D-NOE and 1H NMR chemical shift data obtained for the title oligonucleotides were compared with similar data previously reported [Broido et al. (1985) Eur. J. Biochem. 150, 117-128] for the unmodified "parent" structure, [d(GGAATTCC)]2. The spectroscopically detectable structural perturbations caused by replacement of phosphate oxygen with sulfur were mostly localized within the GsA moiety, and were greater for the Rp configuration wherein sulfur is oriented into the major groove of the B-helix. UV-derived Tm measurements gave the following order of stability for the duplexes in 0.4 M NaCl: unmodified (33.9 +/- 0.1 degrees C) approximately Sp-Sp (34.1 degrees C) greater than Rp-Rp (31.7 degrees C). The title compounds were prepared by a new and convenient synthetic route which utilized HPLC to separate the diastereomeric O-ethyl phosphorothioate precursors, (Rp)- and (Sp)-d[GG(S,Et)AATTCC], for subsequent de-ethylation by ammonia in water.

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Year:  1986        PMID： 3786144      PMCID： PMC311930          DOI： 10.1093/nar/14.22.9081

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN： 0305-1048            Impact factor:   16.971


  34 in total

1.  Investigation of the solution structure of a DNA octamer [d(GGAATTCC)]2 using two-dimensional nuclear Overhauser enhancement spectroscopy.

Authors:  M S Broido; T L James; G Zon; J W Keepers
Journal:  Eur J Biochem       Date:  1985-07-01

2.  The stereochemical course of the restriction endonuclease EcoRI-catalyzed reaction.

Authors:  B A Connolly; F Eckstein; A Pingoud
Journal:  J Biol Chem       Date:  1984-09-10       Impact factor: 5.157

3.  Complete assignment of the non-exchangeable proton nmr resonances of [d-(GGAATTCC)]2 using two-dimensional nuclear overhauser effect spectra.

Authors:  M S Broido; G Zon; T L James
Journal:  Biochem Biophys Res Commun       Date:  1984-03-15       Impact factor: 3.575

4.  Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach.

Authors:  J E Marugg; C van den Bergh; M Tromp; G A van der Marel; W J van Zoest; J H van Boom
Journal:  Nucleic Acids Res       Date:  1984-12-11       Impact factor: 16.971

5.  Sequence-specific recognition of DNA: assignment of nonexchangeable proton resonances in the consensus Pribnow promoter DNA sequence by two-dimensional NMR.

Authors:  D E Wemmer; S H Chou; D R Hare; B R Reid
Journal:  Biochemistry       Date:  1984-05-08       Impact factor: 3.162

6.  Bond order and charge localization in nucleoside phosphorothioates.

Authors:  P A Frey; R D Sammons
Journal:  Science       Date:  1985-05-03       Impact factor: 47.728

7.  Recognition by restriction endonuclease EcoRI of deoxyoctanucleotides containing modified sugar moieties.

Authors:  E Ohtsuka; Y Ishino; K Ibaraki; M Ikehara
Journal:  Eur J Biochem       Date:  1984-03-15

8.  Synthesis and characterization of an octanucleotide containing the EcoRI recognition sequence with a phosphorothioate group at the cleavage site.

Authors:  B A Connolly; B V Potter; F Eckstein; A Pingoud; L Grotjahn
Journal:  Biochemistry       Date:  1984-07-17       Impact factor: 3.162

9.  Reversed-phase high-performance liquid chromatographic separation of diastereomeric phosphorothioate analogues of oligodeoxyribonucleotides and other backbone-modified congeners of DNA.

Authors:  W J Stec; G Zon; B Uznanski
Journal:  J Chromatogr       Date:  1985-06-19

10.  Evidence for sequence-specific conformational changes in DNA from the melting temperatures of DNA phosphorothioate derivatives.

Authors:  J W Suggs; D A Taylor
Journal:  Nucleic Acids Res       Date:  1985-08-12       Impact factor: 16.971
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  21 in total

1.  Oligonucleotides with conjugated dihydropyrroloindole tripeptides: base composition and backbone effects on hybridization.

Authors:  I V Kutyavin; E A Lukhtanov; H B Gamper; R B Meyer
Journal:  Nucleic Acids Res       Date:  1997-09-15       Impact factor: 16.971

2.  The estimation of distances between specific backbone-labeled sites in DNA using fluorescence resonance energy transfer.

Authors:  H Ozaki; L W McLaughlin
Journal:  Nucleic Acids Res       Date:  1992-10-11       Impact factor: 16.971

3.  Unusual duplex formation in purine rich oligodeoxyribonucleotides.

Authors:  W D Wilson; M H Dotrong; E T Zuo; G Zon
Journal:  Nucleic Acids Res       Date:  1988-06-10       Impact factor: 16.971

4.  Inhibition of HIV-LTR gene expression by oligonucleotides targeted to the TAR element.

Authors:  T Vickers; B F Baker; P D Cook; M Zounes; R W Buckheit; J Germany; D J Ecker
Journal:  Nucleic Acids Res       Date:  1991-06-25       Impact factor: 16.971

5.  Synthesis and characterization of a substrate for T4 endonuclease V containing a phosphorodithioate linkage at the thymine dimer site.

Authors:  T Murata; S Iwai; E Ohtsuka
Journal:  Nucleic Acids Res       Date:  1990-12-25       Impact factor: 16.971

6.  Duplex stabilities of phosphorothioate, methylphosphonate, and RNA analogs of two DNA 14-mers.

Authors:  L Kibler-Herzog; G Zon; B Uznanski; G Whittier; W D Wilson
Journal:  Nucleic Acids Res       Date:  1991-06-11       Impact factor: 16.971

7.  Comparative inhibition of chloramphenicol acetyltransferase gene expression by antisense oligonucleotide analogues having alkyl phosphotriester, methylphosphonate and phosphorothioate linkages.

Authors:  C J Marcus-Sekura; A M Woerner; K Shinozuka; G Zon; G V Quinnan
Journal:  Nucleic Acids Res       Date:  1987-07-24       Impact factor: 16.971

8.  Synthetic repeating sequence DNAs containing phosphorothioates: nuclease sensitivity and triplex formation.

Authors:  L J Latimer; K Hampel; J S Lee
Journal:  Nucleic Acids Res       Date:  1989-02-25       Impact factor: 16.971

9.  Phosphorothioate analogs of oligodeoxynucleotides: inhibitors of replication and cytopathic effects of human immunodeficiency virus.

Authors:  M Matsukura; K Shinozuka; G Zon; H Mitsuya; M Reitz; J S Cohen; S Broder
Journal:  Proc Natl Acad Sci U S A       Date:  1987-11       Impact factor: 11.205

10.  An approach to the stereoselective synthesis of Sp-dinucleoside phosphorothioates using phosphotriester chemistry.

Authors:  R Cosstick; D M Williams
Journal:  Nucleic Acids Res       Date:  1987-12-10       Impact factor: 16.971
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