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  • 1
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Several 15N enriched oximes of heterocyclic aldehydes have been prepared in syn and anti forms. The less stable form may be obtained by UV irradiation of the other one. The geminal 15N—H coupling in the R—CH=15N—OH fragment allows an immediate and unambiguous assignment of the configuration to be made, being 13 to 16 Hz and 2 to 3 Hz for the anti and syn forms, respectively. Whereas oximes 1 to 4 are preferentially in the anti form, the N-methylpyridinium aldoxime iodides (2-PAM, 3-PAM, 4-PAM) are found to be syn in the stable form and not anti as previously thought. This reassignment is of special interest, since 2-PAM (8), which is an excellent antidote against alkyl phosphate nerve poisoning, has been used to study the geometry of the acetylcholinesterase active site of the enzyme.
    Notes: Plusieurs oximes, enrichies en 15N, d'aldéhydes hétérocycliques ont été préparées dans les formes syn et anti. La forme la moins stable peut être obtenue par irradiation UV de l'autre. Le couplage géminal 15N—H dans le fragment R—CH=15N—OH permet une attribution non ambiguë de la configuration; il est de 13 à 16 Hz et de 2 à 3 Hz pour les formes anti et syn, respectivement. Les oximes 1 à 4 sont préférentiellement anti, alors que la forme stable des oximes des aldéhydes de N-méthyl pyridinium (8 à 11) est syn et non pas anti comme cela avait été admis. Cette réattribution présente un intérêt spécial puisque 2-PAM (8), qui est un excellent antidote réactivant l'acétylcholinestérase inhibée par phosphorylation, a été utilisée pour étudier la géometrie du site actif de l'enzyme.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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