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  • 1
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 1075-1092 
    ISSN: 0170-2041
    Schlagwort(e): Artificial phosphodiesterase ; Naphthalene, 1,8-disubstituted ; Molecular Recognition ; Staphylococcal nuclease, model of ; Enzymes ; Amidinium phosphate ; Ion-Pair Complexes ; Guanidine ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Supramolecular Phosphoryl Transfer Reactions Mediated by Amidinium Phosphate Ion-Pair ComplexesIn order to build up simplified synthetic models of staphylococcal nuclease two derivatives of 8-phenylnaphthalene-1-carboxamidine equipped with nucleophilic side chains have been prepared (1,2). After protonation these amidinium alcohols bind phosphodiester anions via hydrogen bonds and react within the ion-pair complexes to give zwitterionic products 27 and 28. The rate accelerations (DMF, 30°C) compared to the phosphorylation of noncharged alcohols are 2700-fold (2) and 930-fold (1).
    Zusätzliches Material: 6 Ill.
    Materialart: Digitale Medien
    Bibliothek Standort Signatur Band/Heft/Jahr Verfügbarkeit
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  • 2
    Digitale Medien
    Digitale Medien
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 49-58 
    ISSN: 0170-2041
    Schlagwort(e): Catalysis ; Guanidine ; Ion pair ; Phosphoric acid diester ; Staphylococcal nuclease, model of ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Acceleration of Substitution Reactions of a Phosphoric Acid Diester by Bis(guanidinium) CompoundsIon-pair coordination of phosphoric acid diesters with positively charged guanidines may cause large rate accelerations in substitution reactions. Here we present a comparative study on the catalytical influence of several mono- bis- and tris(guanidines) and of other cationic compounds. Large rate effects occur if 1,3-bis(aminomethyl)benzene or 1,2-ethylenediamine are used as spacers. Further acceleration can be achieved by exchanging guanidinium groups by 2-aminoimidazolines. The 4800-fold rate enhancement seen in the best case demonstrates the importance of the bis(guanidinium) moiety of staphylococcal nuclease and gives good perspectives towards future uses of guanidinium compounds as RNA cleaving agents.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    Bibliothek Standort Signatur Band/Heft/Jahr Verfügbarkeit
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