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Research Article Open access CC BY 4.0

Ring-Opening of Cyclodextrins: An Efficient Route to Pure Maltohexa-, Hepta-, and Octaoses

Matthieu Pélingre, Dindet Steve-Evanes Koffi Teki, Jamal El-Abid, Vincent Chagnault, José Kovensky, Véronique Bonnet

Organics · pp. 287–305 · Published 25 Aug 2021

10.3390/org2030015

Abstract

Many preparations of maltooligosaccharides have been described in literature, essentially using enzymatic or biotechnological processes. These compounds, derived from starch, are well-known as prebiotic agents. The use of maltohexa-, hepta-, and octaoses as synthons in organic synthesis was also well documented in literature. They can indeed be obtained as single compounds by the cyclodextrins’ ring-opening. This reaction has been studied for many years, varying the protecting and functional groups and the reaction conditions, leading to functionalized oligomaltoses. These compounds are of wide interest in various fields. They have a strong potential as scaffolds for multivalence in chemobiology, as building blocks for the production of biomimetic pseudo-glycopeptides, as well as monomers for the preparation of materials. In view of the importance of these oligomaltoses, this review focuses on the different methodologies allowing access to them via chemical and enzymatic ring-opening of cyclodextrins.

Synthon Ring (chemistry) Monomer Chemistry Combinatorial chemistry Organic chemistry Organic synthesis Catalysis

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