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  • oligonucleotides  (3)
  • 5-(thien-2-yl) uracil analogs  (1)
  • 1
    Electronic Resource
    Electronic Resource
    5-(thien-2-yl) uracil analogs: 5-(5-methylthien-2-yl)-2′-deoxyuridine, 5-(5-thien-2-yl)-2′-deoxyuridine, and 5-(5-bromothien-2-yl)-2′-deoxyuridine (1996)
    Springer
    Journal of chemical crystallography 26 (1996), S. 777-789 
    Details
    ISSN: 1572-8854
    Keywords: XRD ; nucleoside ; 5-(thien-2-yl) uracil analogs ; dimeric bonds ; coplanarity ; HSV-1
    Source: Springer Online Journal Archives 1860-2000
    Topics: Geosciences , Physics
    Notes: Abstract Crystal structures of 5-(5-methylthien-2-yl)-2′-deoxyuridine (I), 5-(5-thien-2-yl)-2′-deoxyuridine (II) and 5-(5-bromothien-2-yl)-2′-deoxyuridine (III) have been obtained from data collected on a four-circle Enraf-Nonius diffractometer (CAD-4 system). Space group, unit/cell parameters and finalR indices are:I, monoclinic,P21,a=9.105(2),b=20.819(2),c=7.932(2) Å, β=98.79(2)°,R=5.7%;II, monoclinic,P21,a=8.720(4),b=20.793(4),c=7.884(4) Å, β=95.06(2)°,R=5.8%;III, monoclinic,P21,a=9.260(2),b=41.655(7),c=7.926(2) Å, β=97.996(13)°,R=9.4%. Structural properties of the title compounds are compared with those of 5-(5-chlorothien-2-yl)-2′-deoxyuridine (IV) previously reported in order to explain their affinity for HSV-1 thymidine kinase and their eventual interaction with viral DNA polymerase. The main structural features observed are the coplanarity of the uracil and thienyl cycles stabilized by a S−O intramolecular interaction and the formation of dimeric intermolecular H bonds between two uracil moieties.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01664656
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  • 2
    Electronic Resource
    Electronic Resource
    Oligonucleotide Analogues with 4-Hydroxy-N-Acetylprolinol as Sugar Substitute (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1997-2010 
    Details
    ISSN: 0947-6539
    Keywords: antisense agents ; chiral recognition ; oligonucleotides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Modified oligonucleotides incorporating trans-4-hydroxy-N-acetyl-L-prolinol (trans-4-HO-L-NAP) or its D-analogue as sugar substitute were synthesised with adenine and thymine as nucleobases. All-adenine oligonucleotides built from (2S,4S) or (2R,4R)-cis-4-hydroxy-N-acetylprolinol were likewise prepared. Hybridisation studies revealed that heterocomplexes formed between polyU and homochiral trans-4-hydroxy-N-acetylprolinol-based oligomers of the same as well as of opposite chirality (polyU/trans-DA*13 and polyU/trans-LA*13). The former, however, were triple-stranded. Other complexes with ribonucleic acids were polyA/trans-LT*13 and polyU/cis-LA*13. Heteroduplexes with deoxynucleic acids were formed between trans-LA*13 and oligothymidylate. Interaction was also observed for cis-LA*13 and oligothymidylate, but not with the D-hydroxyprolinol analogues. Microcalorimetry proved this interaction to be the formation of a triple-stranded complex. Two heteroduplexes, trans-LA*13/dT13 and trans-LA*13/polyU, had similar or slightly increased stability when compared to the natural dA13/dT13 or dA13/polyU systems. Microcalorimetry clearly indicated the formation of a duplex, in contrast to interactions with N-acetylprolinol oligonucleotides of different stereochemistry. Moreover, the enthalpy change was of the same magnitude but the association constant was slightly lower. Natural nucleic acids thus clearly prefer hybridisation with L-hydroxyprolinol oligomers over D-hydroxyprolinol oligomers. For the series investigated, the L-trans oligomers (Figure 1) seem best to mimic natural oligonucleotides. These modified oligonucleotides formed homocomplexes if both strands were of the same chirality, that is, homocomplexes formed between trans-LA* and trans-LT* and between trans-DA* and trans-DT*, reflecting the isochiral pu-py pairing found in natural nucleic acids. Once more, however, calorimetry proved these to be triplex interactions. Heterochiral pairing was not observed between modified oligonucleotides, but only between modified oligonucleotides and natural polyU. The thermal stabilities of these heterochiral complexes differed clearly.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970031215
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  • 3
    Electronic Resource
    Electronic Resource
    1′,5′-Anhydrohexitol Oligonucleotides: Hybridisation and Strand Displacement with Oligoribonucleotides, Interaction with RNase H and HIV Reverse Transcriptase (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1513-1520 
    Details
    ISSN: 0947-6539
    Keywords: duplex ; gel mobility ; nucleic acids ; oligonucleotides ; strand displacement ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hexitol nucleic acids (HNAs) with four natural bases form stable and sequence-selective duplexes with RNA. This was investigated by Tm determinations and gel shift experiments. The CD spectra of an HNA-RNA duplex show similarities with the CD spectra of the A-form of dsRNA. Single-stranded HNAs are able to induce strand displacement in a double-stranded RNA sequence. An HNA-RNA duplex is a poor substrate for RNase H, and can inhibit the RNase H-mediated cleavage of a natural DNA-RNA substrate. The HNA-RNA hybrid enhances the activity of HIV reverse transcriptase.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030920
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  • 4
    Electronic Resource
    Electronic Resource
    1′, 5′ -Anhydrohexitol Oligonucleotides: Synthesis, Base Pairing and Recognition by Regular Oligodeoxyribonucleotides and Oligoribonucleotides (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 110-120 
    Details
    ISSN: 0947-6539
    Keywords: antisense systems ; DNA recognition ; nucleic acids ; oligonucleotides ; RNA ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oligonucleotides constructed of 1′, 5′-anhydrohexitol nucleoside building blocks (hexitol nucleic acids, HNA) are completely stable towards 3′-exonuclease and form very stable self-complementary duplexes as well as sequence-selective stable duplexes with the natural DNA and RNA. Triple-helix formation has also been observed. These hybridisation characteristics are highly dependent on the base sequence and the experimental conditions. When using a phosphate buffer containing 0.1M NaCl, a homopurine HNA dodecamer gives a δTm of +3.0 °C/ base pair with RNA as complement. These oligomers may therefore be of considerable interest as antisense constructs.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030118
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