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  • oligonucleotides  (2)
  • Nucleosides  (1)
  • Polymer and Materials Science  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Polymer-linked acycloguanosine (1984)
    New York : Wiley-Blackwell
    Die Makromolekulare Chemie 185 (1984), S. 687-695 
    Details
    ISSN: 0025-116X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Polymer-linked 9-(2-hydroxyethoxymethyl)guanine (1) (acycloguanosine, acyclovir®) was prepared. Condensation of 1 with succinic anhydride gave in 77% yield 2-(9-guanylmethoxy)-ethyl hydrogen succinate (2), which was coupled through its carboxylic group either to poly(L-lysine) (M̄r = 55000) or to N-(6-aminohexyl)carbamoylmethylated dextran T80 to yield the polymers 3 and 4 (ligand concentrations in 3: 30 - 48 μmol of 2/g, in 4: 100 - 171 μmol of 2/g). From both polymers the antiviral 1 could be released by controlled saponification; the rate of drug delivery was found to be a function of pH and temperature. The polymeric carrier system 3 was degraded by endo-dextranase, and the carrier system 4 by trypsin, yielding low-molecular-weight derivatives of the pharmacon.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/macp.1984.021850407
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  • 2
    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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  • 3
    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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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of 2′-Azido-2′,3′-didehydro-2′,3′-dideoxythymidine (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 513-519 
    Details
    ISSN: 0170-2041
    Keywords: Thymidine derivatives ; Azides ; HIV ; Carbohydrates ; Nucleosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Compound 15 - the 2′-azido analog of the anti-HIV compound 2′,3′-didehydro-2′,3′-dideoxythymidine - was synthesized. Treatment of 5′-O-trityl-β-D-ribofuranosylthymine (1) with DAST or MSTF gave the 2,2′-anhydro derivative 2. The latter and its 3′-O-benzoate 3 were used for the synthesis of the 2′-azido-2′-deoxy derivatives 4 and 5. Two routes to the synthesis of 15 from 5 were investigated. (i) Treatment of 5 with DAST gave a mixture of the 5′-O-trityl derivatives 12 and 13 as well as 1-(2-azido-2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)thymine (16) along with 2,3′-anhydro derivative 14 (2%). Detritylation of the mixture yielded 15 (39%) and 16 (12%). (ii) Mesylation of 5 gave 17 which yielded 15 upon saponification and detritylation. Compound 15 showed moderate inhibitory activity against HIV-1 and HIV-2 in MT-4 cells.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930185
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