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Iminosugars: From Synthesis to Therapeutic Applications

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The field of iminosugars is a very exciting area of research. These carbohydrate mimetics were first imagined and synthesized by chemists in the 1960s before being isolated from Nature a few years later. Since the discovery of their biological activity as potent glycosidase inhibitors in the 1970s, iminosugars have been the subject of intense studies at the interface between organic synthesis, glycobiology and medicinal science. In 1999, Arnold Stütz edited the first book devoted to iminosugars (Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, Wiley-VCH, New York; 1999). The title of this outstanding monograph reflected the main features of the field at that time and the strong interplay between isolation of natural products such as nojirimycin, synthesis and biochemical research. However, the most striking word of the title is undoubtedly the preposition ‘beyond’ which was premonitory. The pace of discovery in the area of iminosugars has indeed increased spectacularly over the past decade. The scope of their biological activity has been extended to the inhibition of numerous proteins including enzymes acting on sugars (glycosyltransferases, glycogen phosphorylases, nucleoside-processing enzymes, UDP-Galp mutase) but also metalloproteinases. GlysetTM and ZavescaTM, the two first examples of iminosugar-based drugs, have been commercialized for complications associated with diabetes and for the treatment of Gaucher’s disease, respectively. New biological and medicinal applications are being uncovered almost every month!

Iminosugars form undoubtedly the most attractive of carbohydrate mimics reported so far. In these structures, the substitution of the endocyclic oxygen of sugars by a basic nitrogen atom leads to remarkable biological properties and raises many challenges in organic synthesis. Since the discovery of their biological activity as glycosidase inhibitors in the 1970’s, these polyvalent molecules have progressively made their way from the laboratory to the clinic.

The impressive series of discoveries in the field over the past ten years indicates clearly that it is “a boom time” for iminosugar chemistry and biology. The scope of their profile as inhibitors has been extended to a number of enzymes such as phosphorylases, glycosyltransferases or metalloproteinases, and iminosugars now constitute lead compounds for the development of new therapeutic agents for a wide range of diseases including diabetes, viral infections, lysosomal storage disorders and tumor metastasis.

Latest developments, from iminosugar synthesis to their use in clinical studies, are presented in this book, which contains contributions from over fifteen of the major chemists, biochemists and drug developers in this rapidly expanding field. An extensive table correlating the structures of more than 600 iminosugars of therapeutic interest with their biological activities is also included in the book and should prove particularly useful to aid with the design and the discovery of novel bioactive substances.

Iminosugars: From Synthesis to Therapeutic Application provides a unique resource for academic and industrial researchers working in the field of iminosugars and glycomimetics of biological and/or therapeutic interest: organic chemists, medicinal chemists, carbohydrate chemists and medical scientists.

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