Semiempirical AM1 and ab initio parameters of the lethal cyclopeptides α-amanitin and its related thioether, S-sulphoxide, sulphone, and o-methyl derivative
The electronic structures and conformational analysis of the toxic cyclopeptides, α-amanitin (I), O-methyl-α-amanitin (II), S-deoxo-α-amanitin (III), α-amanitin-(S)-sulphoxide (IV) and α-amanitin sulphone (V) were obtained for the first time from molecular parameters on the basis of AM1 and ab initi...
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| Autores principales: | , , |
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| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_01661280_v536_n2-3_p243_Pomilio |
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| Sumario: | The electronic structures and conformational analysis of the toxic cyclopeptides, α-amanitin (I), O-methyl-α-amanitin (II), S-deoxo-α-amanitin (III), α-amanitin-(S)-sulphoxide (IV) and α-amanitin sulphone (V) were obtained for the first time from molecular parameters on the basis of AM1 and ab initio methods. Stereochemical changes, total energy, MEPs, MO calculations and dipole moments were calculated. Both semiempirical and ab initio methods have been compared, showing to be in good agreement. Limitations of the methods are discussed in each case. Binding and toxicity can be thus satisfactorily explained by the results, showing that stereochemical as well as electronic factors are involved. © 2001 Elsevier Science B.V. |
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