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Abstract:

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.

Registro:

Documento: Artículo
Título:Semiempirical AM1 and ab initio parameters of the lethal cyclopeptides α-amanitin and its related thioether, S-sulphoxide, sulphone, and o-methyl derivative
Autor:Pomilio, A.B.; Battista, M.E.; Vitale, A.A.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:α-amanitin; α-amanitin sulphone; α-amanitin-(S)-sulphoxide; AM1 and ab initio studies; O-methyl-α-amanitin; S-deoxo-α-amanit in; alpha amanitin; alpha amanitin sulfone; alpha amanitin sulfoxide; amanitin; deoxo alpha amanitin; o methyl alpha amanitin; unclassified drug; Amanita phalloides; article; conformation; dipole; geometry; mathematical computing; stereochemistry; structure analysis; toxin analysis
Año:2001
Volumen:536
Número:2-3
Página de inicio:243
Página de fin:262
DOI: http://dx.doi.org/10.1016/S0166-1280(00)00638-2
Título revista:Journal of Molecular Structure: THEOCHEM
Título revista abreviado:J. Mol. Struct. THEOCHEM
ISSN:01661280
CODEN:THEOD
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01661280_v536_n2-3_p243_Pomilio

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Citas:

---------- APA ----------
Pomilio, A.B., Battista, M.E. & Vitale, A.A. (2001) . Semiempirical AM1 and ab initio parameters of the lethal cyclopeptides α-amanitin and its related thioether, S-sulphoxide, sulphone, and o-methyl derivative. Journal of Molecular Structure: THEOCHEM, 536(2-3), 243-262.
http://dx.doi.org/10.1016/S0166-1280(00)00638-2
---------- CHICAGO ----------
Pomilio, A.B., Battista, M.E., Vitale, A.A. "Semiempirical AM1 and ab initio parameters of the lethal cyclopeptides α-amanitin and its related thioether, S-sulphoxide, sulphone, and o-methyl derivative" . Journal of Molecular Structure: THEOCHEM 536, no. 2-3 (2001) : 243-262.
http://dx.doi.org/10.1016/S0166-1280(00)00638-2
---------- MLA ----------
Pomilio, A.B., Battista, M.E., Vitale, A.A. "Semiempirical AM1 and ab initio parameters of the lethal cyclopeptides α-amanitin and its related thioether, S-sulphoxide, sulphone, and o-methyl derivative" . Journal of Molecular Structure: THEOCHEM, vol. 536, no. 2-3, 2001, pp. 243-262.
http://dx.doi.org/10.1016/S0166-1280(00)00638-2
---------- VANCOUVER ----------
Pomilio, A.B., Battista, M.E., Vitale, A.A. Semiempirical AM1 and ab initio parameters of the lethal cyclopeptides α-amanitin and its related thioether, S-sulphoxide, sulphone, and o-methyl derivative. J. Mol. Struct. THEOCHEM. 2001;536(2-3):243-262.
http://dx.doi.org/10.1016/S0166-1280(00)00638-2