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Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

ABSTRACT: Glycosyl phosphates are shown to be activated to stereospecific nucleophilic substitution reactions by precisely tailored bis-thiourea catalysts. Enhanced reactivity and scope is observed with phosphate relative to chloride leaving groups. Stronger binding (Km) to the H-bond donor and enhanced reactivity of the complex (kcat) enables efficient catalysis with broad functional group compatibility under mild, neutral conditions.

SUBMITTER: Levi SM

PROVIDER: S-EPMC6320501 | biostudies-other | 2019 Jan

REPOSITORIES: biostudies-other

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Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

Levi Samuel M SM Li Qiuhan Q Rötheli Andreas R AR Jacobsen Eric N EN

Proceedings of the National Academy of Sciences of the United States of America 20181217 1

Glycosyl phosphates are shown to be activated to stereospecific nucleophilic substitution reactions by precisely tailored bis-thiourea catalysts. Enhanced reactivity and scope is observed with phosphate relative to chloride leaving groups. Stronger binding (K<sub>m</sub>) to the H-bond donor and enhanced reactivity of the complex (k<sub>cat</sub>) enables efficient catalysis with broad functional group compatibility under mild, neutral conditions. ...[more]

PMID: 30559190

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