Rifamycins: an insight into biological activity based on structural investigations
| Autor: | W. Fedeli, A. Vaciago, S. Cerrini, Mario Brufani |
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| Rok vydání: | 1974 |
| Předmět: |
Models
Molecular Hot Temperature Stereochemistry Molecular Conformation Rifamycins Structure-Activity Relationship chemistry.chemical_compound X-Ray Diffraction Structural Biology Amide polycyclic compounds Anilides Molecular Biology Polymerase biology Computers Rifamycin Biological activity DNA-Directed RNA Polymerases Naphthoquinone Hydroquinones chemistry biology.protein Antibacterial activity Mathematics Derivative (chemistry) Naphthoquinones |
| Zdroj: | Journal of Molecular Biology. 87:409-435 |
| ISSN: | 0022-2836 |
| Popis: | The structures of two compounds of the antibiotic rifamycin series have been studied by X-ray methods: rifamycin B, C 39 H 49 NO 14 , which is active on bacterial RNA polymerase, and rifamycin Y, C 39 H 47 NO 15 , which is devoid of any antibacterial activity. In both cases their p -iodoanilide derivative has been used and the final crystal structure data are now given. A comparative study of the structures of rifamycin B and rifamycin Y, and of the structures of two other ansa -compounds with similar activity on bacterial RNA polymerase, tolypomycin Y and streptovaricin C, together with the analysis of the activity ratios of a series of semisynthetic rifamycins, makes it possible to suggest that the following constitutional and conformational features are common to all the ansa -compounds with anti-bacterial activity: (i) a naphthoquinone or naphthohydroquinone nucleus with free oxygen functions, O(1) and O(2), on C(1) and C(8) respectively: (ii) an amide nitrogen attached to C(2); (iii) a 17-membered chain bridging the chromophoric group; (iv) two free hydroxyl groups attached to atoms C(21) and C(23) of the ansa -bridge and in the same relative positions with respect to each other and with respect to O(1) and O(2). However, the constitution and the conformation of the remaining part of the ansa -bridge can be rather different in different compounds. |
| Databáze: | OpenAIRE |
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