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Hydrolysis of Methylglucosides

Abstract

IN the course of a study of the mechanisms involved in the solvolytic reactions of glycosides, we have investigated the position of bond fission occurring in the hydrolysis of α- and β-D-methylglucosides. The reactions were carried out in water enriched in oxygen-18, and the methanol produced was isolated by fractional distillation in an efficient column, and then pyrolysed to give carbon monoxide which was examined by a mass spectrometer. We have found that the hydrolysis of α- and β-D-methylglucosides both in 1 N acid solution and in the presence of appropriate methylglucosidases proceeds by fission of the hexose–oxygen bond:

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References

  1. Armstrong, J. Chem. Soc., 1305 (1903).

  2. Koshland, Biol. Rev., 416 (1953).

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BUNTON, C., LEWIS, T., LLEWELLYN, D. et al. Hydrolysis of Methylglucosides. Nature 174, 560 (1954). https://doi.org/10.1038/174560a0

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