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Labilization of ester bonds in aminodeoxyinositol derivatives as mediated by molecular conformation

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Zusammenfassung

Eine neue Art von Esterlabilisierung wurde in der Gruppe der Polyacetate tertiärer und (mono)quaternärer Inosamine und Streptamine entdeckt. Im Gegensatz zu den vergleichsweise beständigen Azetaten der quartärencis- undtrans-Dimethylaminocyclohexanole zeigten Penta-O-acetyl-2-desoxy-2-trimethylammoniumscyllitol als auchd,l-Tetra-O-acetyl-1, 3-bisdesoxy-1-dimethylamino-3-trimethylammoniumscyllitol rasche spontane Esterhydrolyse in wässrigem neutralen Medium, die grössenordnungsmässig vergleichbar war mit der unter Einwirkung von Cholinesterase beobachteten hydrolytischen Aktivität des — ohne Enzym beständigen — quartären Pentaacetats in der Myoinositol-Reihe. Offenbar spielt beim Zustandekommen solcher Labilisierungen die Totalkonformation der Molekel eine bisher nicht vermutete Rolle.

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References

  1. H. D. Baldridge, W. J. McCarville, andS. L. Friess, J. Amer. chem. Soc.77, 739 (1955).

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  2. For representative polar-type labilization of quaternary derivativesvia some quasi-cyclic transition state (with greater planarity and stability inscyllo as compared withmyo) such as that in the all equatorial conformation of II, see the analogous postulation on hydrolsis of scopolamine methyl bromide [E. R. Garrett, J. Amer. chem. Soc.79, 1071 (1957);77, 4002 (1955)] and the analogies ofH. B. Henbest et al. [J. chem. Soc.1957, 1965)].

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Authors and Affiliations

  1. National Institute of Arthritis, and Metabolic Diseases, National Institutes of Health, Bethesda, Md.

    G. F. Holland & B. Witkop

  2. Naval Medical Research Institute, Bethesda, Md.

    S. L. Friess

Authors
  1. G. F. Holland
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  2. B. Witkop
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  3. S. L. Friess
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Holland, G.F., Witkop, B. & Friess, S.L. Labilization of ester bonds in aminodeoxyinositol derivatives as mediated by molecular conformation. Experientia 14, 129–130 (1958). https://doi.org/10.1007/BF02157112

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  • DOI: https://doi.org/10.1007/BF02157112

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