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Chemical and enzymatic approaches to the synthesis of cyclic oligosaccharides

Maiti, Krishnagopal and Samanta, Gopal Kumar and Daskhan, Gour Chand and Jayaraman, N (2017) Chemical and enzymatic approaches to the synthesis of cyclic oligosaccharides. [Book Chapter]

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Official URL: https://doi.org/10.1039/9781782626657-00165


Cyclic oligosaccharides, such as naturally-occurring cyclomaltodextrins or cyclodextrins, cycloisomaltooligosaccharides or cyclodextrans, cycloinulooligosaccharides, have attracted a repertoire of interest cutting across various fields, as a result of their immense industrial importance arising from their molecular and supramolecular properties. As opposed to the production of cyclic oligosaccharides biosynthetically in an exquisite manner, their chemical synthesis remains a challenge. Whereas macrocyclization and cyclooligomerization have provided necessary tools to approach their synthesis, modifications in their monosaccharide moieties add further to protract the synthesis overall. Yet significant progress has been made in chemical and enzymatic synthesis during the last three decades, particularly on the synthesis of tailor-made or made-to-order cyclic oligosaccharides. Manifold values of cyclic oligosaccharide macrocycles are imminent, resulting from their reduced hydrolytic rates to hydrophobic cavities, backbone modifications assume even greater importance. Such backbone modified cyclic oligosaccharides have been demonstrated to alter functions in several instances. Focusing on synthesis of cyclic oligosaccharides alone, there is a continuous evolution of methods and strategies that facilitate their synthesis. Both chemical and enzymatic routes are fore-runners in the advancements towards fully synthetic cyclic oligosaccharides. This review compiles logical advancements in cyclic oligosaccharide synthesis, particularly over the last decade, with emphasis on modifications of glycosidic bonds or individual sugar moieties.

Item Type: Book Chapter
Publisher: Royal Society of Chemistry
Additional Information: The Copyright of this article belongs to the Royal Society of Chemistry
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Jun 2022 05:51
Last Modified: 03 Jun 2022 05:51
URI: https://eprints.iisc.ac.in/id/eprint/72963

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