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Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives.

ABSTRACT: Thioglycosides are more resistant to enzymatic hydrolysis than their O-linked counterparts, thereby becoming attractive targets for carbohydrate-based therapeutic development. We report the first development of methods for the site-selective incorporation of S-linkages into automated solution-phase oligosaccharide protocols. The protocols were shown to be compatible with the formation of S- or O-glycosides for the synthesis of mannopyranoside trimmers that incorporate both S- and O-linkages to allow the selective incorporation of an S-glycoside in various stages in an automated program.

SUBMITTER: Kern MK

PROVIDER: S-EPMC7493207 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives.

Kern Mallory K MK Pohl Nicola L B NLB

Organic letters 20200520 11

Thioglycosides are more resistant to enzymatic hydrolysis than their O-linked counterparts, thereby becoming attractive targets for carbohydrate-based therapeutic development. We report the first development of methods for the site-selective incorporation of S-linkages into automated solution-phase oligosaccharide protocols. The protocols were shown to be compatible with the formation of S- or O-glycosides for the synthesis of mannopyranoside trimmers that incorporate both S- and O ...[more]

PMID: 32432478

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