Small-Molecule Catalysts for the Stereoselective Synthesis of Oligosaccharides
用于立体选择性合成低聚糖的小分子催化剂
基本信息
- 批准号:9327315
- 负责人:
- 金额:$ 28.21万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:2015
- 资助国家:美国
- 起止时间:2015-07-15 至 2018-12-31
- 项目状态:已结题
- 来源:
- 关键词:AddressAffectAlcoholsAminesBindingBiomimeticsCarbohydratesCatalysisChemicalsChloride IonChloridesComplexCouplingDevelopmentDisaccharidesGenerationsGleanGlycoconjugatesGlycolipidsGlycopeptidesGlycoproteinsGlycosidesGoalsHealthHumanHydrogen BondingKineticsLaboratoriesLibrariesLinkLipidsMethodologyMethodsModelingNatureNucleotidesOligosaccharidesPeptidesPhasePhenolsPolynucleotidesPolysaccharidesPositioning AttributePreparationProductionPropertyProteinsProtocols documentationReactionRoleScienceSeriesSiteSolidStagingStructureSystemTechnologyThioureaWorkalkalinityanalogbasecarbonyl groupcatalystcomputer studiescost effectivedesignglycosylationglycosyltransferaseimprovedinterestmicrobialmilligrampolypeptidesmall moleculesugar
项目摘要
DESCRIPTION (provided by applicant): This project has as its aim the development of robust, practical, and general methods for glycosylating nucleophiles with predictable stereoselectivity. Our laboratory has helped pioneer the use of small-molecule chiral H-bond donors as catalysts for enantioselective reactions. As an extension of these studies, we have uncovered a new principle for effecting selective glycosylation reactions. Precisely designed macrocyclic bis-thiourea catalysts promote stereospecific, invertive reactions of alcohol nucleophiles with glycosyl chlorides. Because glycosyl chlorides are quite stable and exist predominantly and often exclusively in the a-configuration, this mode of catalysis represents a widely applicable solution to the creation of ß-glycosidic linkages. We will seek to explore the scope and limitations of the macrocylic catalysts devised thus far in the context of model disaccharide couplings and the synthesis representative biologically important oligosaccharides. The rate of glycosylation is correlated to the Lewis basicity of the carbonyl group on the catalyst, and our current mechanistic hypothesis invokes a functional role for this moiety as a general base to activate the acceptor nucleophile in a manner that mimics invertive glycosyltransferases. We will carry out a systematic mechanistic study of the catalytic reaction in order to ascertain whether a biomimetic general-base mechanism is indeed operative, and to identify the optimal nature and position of the Lewis base component for maximum reactivity and scope. We will also explore whether this cooperative activation mechanism might be extended to the design of catalysts that promote a-selective glycosylations via doubly invertive substitutions. If developed fully and successfully, this methodology would enable the synthesis of complex oligosaccharides in a programmable manner that could be applied by non-specialists, and also allow the production of biomedically relevant glycans, glycopeptides, glycoproteins, glycolipids, and microbial polysaccharides and glycoconjugates on a practical scale.
项目成果
期刊论文数量(0)
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科研奖励数量(0)
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专利数量(0)
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ERIC N JACOBSEN其他文献
ERIC N JACOBSEN的其他文献
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{{ truncateString('ERIC N JACOBSEN', 18)}}的其他基金
Development, Elucidation, and Application of New Principles in Stereoselective Catalysis
立体选择性催化新原理的开发、阐明和应用
- 批准号:
10622995 - 财政年份:2023
- 资助金额:
$ 28.21万 - 项目类别:
Broadly Applicable, Small Molecule Catalysts for Stereoselective and Site-Selective Glycosylation Reactions
适用于立体选择性和位点选择性糖基化反应的广泛适用的小分子催化剂
- 批准号:
9900832 - 财政年份:2019
- 资助金额:
$ 28.21万 - 项目类别:
Broadly Applicable, Small Molecule Catalysts for Stereoselective and Site-Selective Glycosylation Reactions
适用于立体选择性和位点选择性糖基化反应的广泛适用的小分子催化剂
- 批准号:
10341140 - 财政年份:2019
- 资助金额:
$ 28.21万 - 项目类别:
Small-Molecule Catalysts for the Stereoselective Synthesis of Oligosaccharides
用于立体选择性合成低聚糖的小分子催化剂
- 批准号:
8985298 - 财政年份:2015
- 资助金额:
$ 28.21万 - 项目类别:
Small-Molecule Catalysts for the Stereoselective Synthesis of Oligosaccharides
用于立体选择性合成低聚糖的小分子催化剂
- 批准号:
9528932 - 财政年份:2015
- 资助金额:
$ 28.21万 - 项目类别:
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