Synthesis and properties of DNA oligomers containing an O4-ethylated thymine. d(e4TpA), d(Ape4T), d(Ape4TpA), and d(Tpe4TpT)

Buchko, Garry W.; Hruska, Frank E.; Sadana, Krishan L.

doi:10.1139/v90-308

Can. J. Chem.

1990

DOI: 10.1139/v90-308

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Synthesis and properties of DNA oligomers containing an O4-ethylated thymine. d(e⁴TpA), d(Ape⁴T), d(Ape⁴TpA), and d(Tpe⁴TpT)

Garry W. Buchko¹,

Frank E. Hruska²,

Krishan L. Sadana³

Abstract: . Can. J. Chem. 68, 201 1 (1990). Syntheses via the phosphotriester method are described for DNA oligonucleotides containing 04-ethylated thymine (e4Thy) and adenine (Ade) bases, d ( e V p~) , d (e) , and ~( A~~V~A ) , for their unmodified analogs, d(TpA), d(ApT), and d(ApTpA), and for d(TpeVpT). 'H NMR chemical shift data obtained from 10 to 70°C at 300 and 500 MHz show that these molecules form right-handed minihelices at low temperature in aqueous solution; the presence of the 04-ethyl group does not se… Show more

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Cited by 2 publications

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References 27 publications

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“…Peaks on the diagonal are truncated to 2% (B-F,K) or 20% (G-J) of their full height. Regions of spectra within 0.1 ppm of the residual HOD signal are set to zero.and oligonucleotides containing modified bases may be obtained from the sum of 3 JHI'H 2 ' plus 3 JHI'H 2 " (1:1') using the equation: %S = (1:1'-9.8)/5.9(10,13,37,(39)(40)(41)(42).…”

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Characterization of γ-Radiation Induced Decomposition Products of Thymidine-Containing Dinucleoside Monophosphates by Nuclear Magnetic Resonance Spectroscopy

Baleja

Buchko²,

Weinfeld³

et al. 1993

Journal of Biomolecular Structure and Dynamics

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To study the chemical and biochemical influence of loss of base aromaticity, dinucleoside monophosphates containing cis-5R,6S-thymidine glycol (Tg) and 5R and 5S 5,6-dihydrothymidine (Th) were prepared from d-ApT and d-TpA by KMnO4 oxidation and rhodium-catalysed hydrogenation, respectively. One and two dimensional 1H NMR techniques were used to characterize the solution conformation of each of the modified dinucleoside monophosphates for comparison with the unmodified compounds. Coupling constant data show that all sugar moieties adopt a predominantly 2'-endo conformation. Estimates of proton-proton distances from two-dimensional NOE experiments reveal that most of the glycosidic bonds prefer the anti conformation. Analysis of the C5'-C4' (gamma) torsion angle of the hydroxymethyl group using 3JH4'H5' and 3JH4'H5" data indicate that these modifications to thymine have little effect on the gamma conformer populations. Although, in general, additions at C5 and C6 of thymine in d-ApT and d-TpA profoundly distort the pyrimidine, they do not otherwise significantly alter the conformation of these compounds relative to the unsubstituted dinucleoside monophosphates. The one exception is the thymine glycol of d-TgpA, which appears to have a higher syn population than the parent compound.

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confidence: 99%

Characterization of γ-Radiation Induced Decomposition Products of Thymidine-Containing Dinucleoside Monophosphates by Nuclear Magnetic Resonance Spectroscopy

Baleja

Buchko²,

Weinfeld³

et al. 1993

Journal of Biomolecular Structure and Dynamics

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The Evaluation OF 2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl Nucleosides as Potential Antisense Constructs: Synthesis, Biophysical Properties and Enzymatic Stability of 2′-Deoxyadenosine-(3′–6′)-[1-(2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl)thymine] Phosphate

Tari¹,

Sadana²,

Secco³

1995

Nucleosides and Nucleotides

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l-(2',3'-dideoxy-~-D-e~~~~~-hex-2'-enop~anosyl)thymine was used as a nucleoside substitute in the synthesis of the dimer APT*. CD studies on the dimer show that it adopts stacked, B-form mini-helices in solution. The title compound, relative to natural APT, possesses an increased resistance to degradation by nucleases. IntroductionIn recent years, the use of antisense constructs as a potential therapeutic tool has received much attention. A major problem with this approach, however, is the rapid enzymatic degradation of natural oligodeoxynucleotides. Therefore, enzymatically stable oligonucleotide analogues that form stable duplexes with their natural complements must be developed. While extensive studies have been carried out on oligonucleotides modified in their bases and phosphate backbones, sugar modifications have only received a small amount of attention. In several redent studies by Augustyns el al.12, the effects on basepairing properties and enzymatic stability of the incorporation of fully saturated hexose nucleoside analogues into antisense oligonucleotides have been examined. While &e modified hexose nucleosides studied conferred greater resistance against enzymatic degradation when incorporated at various positions in natural oligonucleotide strands, they suffered from a reduced duplex-forming capacity with the natural complement. In addition to possible steric pro%lems, a second deterrent to duplex formation is the decrease in entropy (due to the loss of conformational freedom) when an oligonucleotide containing flexible hexose sugars binds to its natural complement. Therefore, assuming the presence of identical intermolecular forces in duplex formation, complexation between single strands

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Synthesis and properties of DNA oligomers containing an O4-ethylated thymine. d(e⁴TpA), d(Ape⁴T), d(Ape⁴TpA), and d(Tpe⁴TpT)

Cited by 2 publications

References 27 publications

Characterization of γ-Radiation Induced Decomposition Products of Thymidine-Containing Dinucleoside Monophosphates by Nuclear Magnetic Resonance Spectroscopy

Characterization of γ-Radiation Induced Decomposition Products of Thymidine-Containing Dinucleoside Monophosphates by Nuclear Magnetic Resonance Spectroscopy

The Evaluation OF 2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl Nucleosides as Potential Antisense Constructs: Synthesis, Biophysical Properties and Enzymatic Stability of 2′-Deoxyadenosine-(3′–6′)-[1-(2′, 3′-Dideoxy-β-D-Erythro-Hex-2′-Enopyranosyl)thymine] Phosphate

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