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Azaglycomimetics: Natural Occurrence, Biological Activity, and Application

  • Reference work entry
Glycoscience

Abstract

A large number of alkaloids mimicking the structures of monosaccharides or oligosaccharides have been isolated from plants and microorganisms. The sugar mimicking alkaloids with a nitrogen in the ring are called azasugars or iminosugars. Naturally occurring azasugars are classified into five structural classes: polyhydroxylated piperidines, pyrrolidines, indolizidines, pyrrolizidines, and nortropanes. They are easily soluble in water because of their polyhydroxylated structures and inhibit glycosidases because of a structural resemblance to the sugar moiety of the natural substrate. Glycosidases are involved in a wide range of anabolic and catabolic processes, such as digestion, lysosomal catabolism of glycoconjugates, biosynthesis of glycoproteins, and the endoplasmic reticulum (ER) quality control and ER‐associated degradation of glycoproteins. Hence, modifying or blocking these processes in vivo by inhibitors is of great interest from a therapeutic point of view. Azasugars are an important class of glycosidase inhibitors and are arousing great interest for instance as antidiabetics, antiobesity drugs, antivirals, and therapeutic agents for some genetic disorders. This review describes the recent studies on isolation, characterization, glycosidase inhibitory activity, and therapeutic application of azaglycomimetics.

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Abbreviations

DAB:

1,4‑dideoxy-1,4‑imino-d‑arabinitol

DMDP:

1,4‑dideoxy-1,4‑imino-d‑mannitol

DNJ:

1‑deoxynojirimycin

ER:

endoplasmic reticulum

ERAD:

ER-associated degradation

FDA:

US Food and Drug Administration

GSL:

glycosphingolipid

HNJ:

homonojirimycin

IRI:

immunoreactive insulin

NIDDM:

non-insulin-dependent diabetes mellitus

NJ:

nojirimycin

STZ:

streptozotocin

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  1. Faculty of Pharmaceutical Science, Hokuriku University, 920-1181, Kanazawa, Japan

    Naoki Asano

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  1. Naoki Asano
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Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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Asano, N. (2008). Azaglycomimetics: Natural Occurrence, Biological Activity, and Application. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_48

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