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Synthesis and biological activity of N6-{N[(4-azido-3,5,6-trifluoro)-pyridin-2-yl]-2-aminoethyl}-adenosine 5'-monophosphate, a new AMP photoactivatable derivative. Covalent modification of horse liver alcohol dehydrogenase
| Content Provider | Scilit |
|---|---|
| Author | Sicsic, Sames Léonil, Joëlle Goffic, François |
| Copyright Year | 1989 |
| Description | Journal: Journal of Biological Inorganic Chemistry N6-(N-[(4-Azido-3,5,6-trifluoro)pyridin-2-yl]-2-aminoethyl)- adenosine 5'-monophosphate has been synthesized and evidence presented for its structural assignment by ultraviolet and 19F-NMR spectroscopies. Its photolysis was shown to occur within 5 min. This AMP derivative behaves as a competitive inhibitor of NAD+ in horse-liver-alcohol-dehydrogenase-promoted oxidation of ethanol, with a Ki (0.95 mM) comparable to the Ki of AMP (1.9 mM). Moreover it is an activator of the enzyme when nicotinamide ribose is used as the oxidation cofactor. This activation is as good as that promoted by AMP or by the well known 8-azido-AMP. Upon photolysis of this new derivative in the presence of horse liver alcohol dehydrogenase, a covalent enzyme--analogue complex was isolated and assayed as a catalyst in the oxidation of ethanol using nicotinamide ribose as the cofactor. The reaction took place without complementation of AMP, indicating clearly that the AMP analogue is mainly covalently bound in the AMP-binding site, and that the linkage formed between the enzyme and the azido derivative has not dramatically altered the active site of the enzyme. A similar experiment with 8-azido-AMP produced a completely inactive complex. |
| Related Links | http://onlinelibrary.wiley.com/doi/10.1111/j.1432-1033.1989.tb14572.x/pdf |
| Ending Page | 440 |
| Page Count | 6 |
| Starting Page | 435 |
| ISSN | 09498257 |
| e-ISSN | 14321327 |
| DOI | 10.1111/j.1432-1033.1989.tb14572.x |
| Journal | Journal of Biological Inorganic Chemistry |
| Issue Number | 2 |
| Volume Number | 179 |
| Language | English |
| Publisher | Wiley-Blackwell |
| Publisher Date | 1989-02-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: Journal of Biological Inorganic Chemistry Medicinal Chemistry Organic Chemistry Biological Activity Alcohol Dehydrogenase Covalent Modification Horse Liver Liver Alcohol Photoactivatable Derivative New Amp Amp Photoactivatable |
| Content Type | Text |
| Resource Type | Article |
| Subject | Biochemistry Inorganic Chemistry |
