Catalysis and Acceleration of Acyl Transfer by Aminocyclodextrins: A Biomimetic System of Use in Enzyme Modeling and Drug Design
| Autor: | Gregory R. J. Thatcher, Colin G. Ferguson |
|---|---|
| Rok vydání: | 1999 |
| Předmět: |
chemistry.chemical_classification
Drug Cyclodextrins Chemistry media_common.quotation_subject Molecular Mimicry Organic Chemistry Esters Biochemistry Catalysis Kinetics Acceleration Enzyme Models Chemical Drug Design Organic chemistry Physical and Theoretical Chemistry Neutral ph Foscarnet media_common |
| Zdroj: | Organic Letters. 1:829-832 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol9906211 |
| Popis: | [formula: see text] Aminocyclodextrins (ACDs), perfunctionalized at the 6-position with amino groups, bind phosphonoformate (PFA) diesters and accelerate acyl transfer reactions with high efficiency at neutral pH. Aminolysis and esterolysis are accelerated and hydrolysis of PFA diesters is catalyzed by ACDs. PFA diesters have significant antiviral activity. The rapid reactions observed with ACDs show that biological nucleophiles may undergo facile covalent modification by PFA esters at physiological pH, which has significant implications for prodrug and drug design strategies. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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