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The Amadori and Heyns Rearrangements: Landmarks in the History of Carbohydrate Chemistry or Unrecognized Synthetic Opportunities?

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Glycoscience

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 215))

Abstract

The Amadori and Heyns rearrangements have been known to carbohydrate chemists for decades. Following an outline of their historical development, a survey of the biological aspects, applications and alternative approaches will be given. Due to their nature, both reactions suffer from a variety of preparative shortcomings; nonetheless, they are very useful bearing in mind that no protecting group manipulations are required. Naturally occurring rearrangement products can play very important biological roles. For example, in the Maillard reaction cascade, this type of rearrangement reactions appear to be involved in the pathological effects of diabetes, Alzheimer’s disease and aging processes in general. Consequently, alternative means of synthetic access to the corresponding products have also been investigated. Both rearrangements appear to be highly underrated as useful methods for natural products synthesis.

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  1. Glycogroup, Institut für Organische Chemie der Technischen Universität Graz, Stremayrgasse 16, 8010, Graz, Austria

    Tanja M. Wrodnigg & Brigitte Eder

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  1. Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, 8010, Graz, Austria

    Arnold E. Stütz

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Wrodnigg, T.M., Eder, B. (2001). The Amadori and Heyns Rearrangements: Landmarks in the History of Carbohydrate Chemistry or Unrecognized Synthetic Opportunities?. In: Stütz, A.E. (eds) Glycoscience. Topics in Current Chemistry, vol 215. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-44422-X_6

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