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Chemical synthesis of C6-tetrazole ?-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

Miller, Gavin; Dimitriou, Eleni

Chemical synthesis of C6-tetrazole ?-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate Thumbnail


Authors

Eleni Dimitriou



Abstract

<jats:p>Alginate is a biocompatible and industrially relevant polysaccharide that derives many of its important properties from the charged carboxylate groups within its polyuronic acid backbone. The design and inclusion of isosteric replacements for these carboxylates would underpin provision of new oligo-/polysaccharide materials with alternate physicochemical properties. Presented herein is our synthesis of mannuronic acid building blocks, appropriately modified at the carboxylate C6 position with a bioisosteric tetrazole. Thioglycosides containing a protected C6-tetrazole are accessed from a C6-nitrile, through dipolar cycloaddition using NaN<jats:sub>3</jats:sub> with <jats:italic>n</jats:italic>-Bu<jats:sub>2</jats:sub>SnO. We also demonstrate access to orthogonally C4-protected donors, suitable for iterative oligosaccharide synthesis. The development of these building blocks is showcased to access anomeric 3-aminopropyl- and 1-phosphate free sugars containing this non-native motif.</jats:p>

Journal Article Type Letter
Acceptance Date Jun 24, 2021
Online Publication Date Jul 5, 2021
Publication Date Jul 5, 2021
Journal Beilstein Journal of Organic Chemistry
Publisher Beilstein-Institut
Peer Reviewed Peer Reviewed
Pages 1527 - 1532
DOI https://doi.org/10.3762/bjoc.17.110
Keywords alginate; glycosyl 1-phosphate; non-native monosaccharide; tetrazole; uronate
Publisher URL https://www.beilstein-journals.org/bjoc/articles/17/110
Related Public URLs https://doi.org/10.3762/bxiv.2021.25.v1

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