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  • 1
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 2841-2858 
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: To provide suitable monomers for a study designed to synthesize copolymers containing alternating sequences of nucleic acid base pairs, the following electron-donor monomers were synthesized: 9-(2-vinyloxyethyl)adenine, 1-(2-vinyloxyethyl)thymine, and 1-(2-vinyloxyethyl)-cytosine. The following electron-acceptor monomers were also synthesized: 9-(2-maleimidoethyl)adenine, 1-(2-maleimidoethyl)thymine, and 1-(2-maleimidoethyl)cytosine. The methods of synthesis are described along with their characterization by the usual methods, and their physical properties are reported. A variety of novel compounds were required as intermediates in the above identified syntheses. This paper also includes characterization of these compounds and a report of their physical properties.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 3725-3737 
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A study was conducted of the complementary base pair interactions between various pairs of electron-donor monomers, electron-acceptor monomers, homopolymers and alternating copolymers selected from the following group: (1) 9-(2-vinyloxyethyl)adenine; (2) 1-(2-vinyloxyethyl)thymine; (3) 1-(2-vinyloxyethyl)cytosine; (4) 9-(2-maleimidoethyl)adenine; (5) 6-chloro-9-(2-maleimidoethyl)purine; (6) 1-(2-maleimidoethyl)thymine; (7) 1-(2-maleimidoethyl)cytosine; (8) homopolymer of (4); (9) homopolymer of (6); (10) alternating copolymer of (2) and maleic anhydride; (11) alternating copolymer of (2) and (5); and (12) alternating copolymer of (2) and (4). By 1H-NMR, in CDCL3, the base pair interactions between (1) and (2) were shown to be hydrogen bonding, the extent of which was shown by a calculated binding constant, K = 61.81 L/mol. The nature of this interaction was conformed by IR. Neither monomer pairs (1)/(2) nor (4)/(6) exhibited hydrogen bonding in DMSO-d6. However, hydrogen bonding interaction was observed for DMSO-d6 solutions of homopolymers (8) and (9) and for alternating copolymer (12). On the basis of an upfield chemical shift of the 2- and 8-aromatic protons of ademine of (1) in D2O, a partial overlap stacking interaction is proposed. No charge-transfer interactions could be observed by UV between donor-acceptor monomer pairs.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 3715-3724 
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The objective of this project was to utilize the alternating copolymerizability of electrondonor monomers with electron-acceptor monomers to selectively introduce nucleic acid bases into copolymers in a controlled sequence distribution. To this end, maleimide monomers containing the adenine, thymine, cytosine, and 6-chloropurine moieties were converted to their hompolymers. The homopolymer of 1-(vinyloxyethoxy)thymine was also prepared. Alternating copolymers of the adenine maleimide monomer and the corresponding 6-chloropurine maleimide monomer with 1-(vinyloxyethoxy)thymine were prepared. The latter copolymer was converted to the alternating adenine-thymine copolymer by reaction with ammonia. Characterization of the polymers and copolymers via spectroscopic methods and physical measurements confirm their proposed structures. Monomer syntheses and characterization, as well as studies designed to establish the extent and nature of adenine-thymine interactions in the copolymers, are reported in accompanying papers.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 29 (1991), S. 1883-1888 
    ISSN: 0887-624X
    Keywords: guanine containing monomers ; N6-acetylguanine containing monomers ; guanine derivatives ; monomer synthesis ; biomimetic monomers ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of four new monomers containing guanine or a guanine precursor was achieved. These were two isomeric acid ester derivatives of guanine and two isomeric vinyl ether derivatives of N2-acetylguanine. In the case of the synthesis of the guanine acid esters IV and V, it was necessary to prepare first the guanine alcohol derivatives II and III. These N-7 and N-9 isomeric alcohols of guanine were separated by fractional crystallization. Subsequent esterification of these alcohols with maleic anhydride gave the desired products. In the other case, N2-acetylguanine was alkylated with 2-chloroethyl vinyl ether to yield the N-7 and N-9 isomer VI and VII, respectively. These were separated using flash column chromatography.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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