Glycosylation of a Neoglycoprotein by Using Glycosynthase and Thioglycoligase Approaches: The Generation of a Thioglycoprotein

Müllegger, Johannes; Chen, Hong Ming; Warren, R. A. J.; Withers, Stephen G.

doi:10.1002/anie.200503900

Cited by 39 publications

(20 citation statements)

References 30 publications

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“…for thioglycosylation of glycoproteins. [77] Kim et al [78] created a library of thioglycosides, potential chaperones of lysosomal glycosidases, under catalysis by the b-thiogalacto-ligase from Xanthomonas manihotis. The thioglycoligase concept was further extended to thioglycosynthases, double mutants of retaining glycosidases.…”

Section: Thioglycoligases and Thioglycosynthasesmentioning

confidence: 99%

Glycosidases in Carbohydrate Synthesis: When Organic Chemistry Falls Short

Bojarová

Křen

2011

Chimia

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Thanks to the stability, good availability, stereoselectivity and broad substrate specificity, oligosaccharide synthesis catalyzed by glycosidases represents an elegant way to complex carbohydrate structures. Twoapproachestoglycosidasecatalysisarepresented:i)theuseofstructurallymodifiedsubstratesthatcarry variousfunctionalmoietiesinthemolecule,andii)thedesignofmutantglycosidasesvoidofhydrolyticactivity. Productsofglycosidase-catalyzedsynthesisareapplicableinarangeofareassuchasimmunology,therapyof Alzheimer'sorParkinson'sdiseasesandthesynthesisofneoglycoproteins.

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Section: Thioglycoligases and Thioglycosynthasesmentioning

confidence: 99%

Glycosidases in Carbohydrate Synthesis: When Organic Chemistry Falls Short

Bojarová

Křen

2011

Chimia

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“…8 ). These engineered GHs were already successfully applied to the biocatalysed synthesis of thiodi- or -trisaccharides [ 68 – 72 ], neo-thioglycoprotein [ 73 ], or even simple thioglycosides with potent inhibitory properties [ 74 ]. More complex biomolecules were also obtained like glycans or glycopolymers [ 75 ], or even rarer thiofuranosides [ 76 ].…”

Section: Reviewmentioning

confidence: 99%

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

Ati

Lafite

Daniellou

2017

Beilstein J. Org. Chem.

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Carbohydrate related enzymes, like glycosyltransferases and glycoside hydrolases, are nowadays more easily accessible and are thought to represent powerful and greener alternatives to conventional chemical glycosylation procedures. The knowledge of their corresponding mechanisms has already allowed the development of efficient biocatalysed syntheses of complex O-glycosides. These enzymes can also now be applied to the formation of rare or unnatural glycosidic linkages.

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“…However, nucleophilic acceptors, such as thiosugars, are able to attack the anomeric center, resulting in the formation of a thioglycosidic linkage. Thio‐linked glycans have been used to produce an array of molecules, such as thioxylosides, beta‐galactosidase inhibitors, a thioglycoprotein, and substrates for enzyme activity tests …”

Section: Thioglycoligasesmentioning

confidence: 99%

Synthesis of Glycans and Glycopolymers Through Engineered Enzymes

Armstrong

Withers

2013

Biopolymers

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The synthesis of defined glycans enables us to further understand their roles in a biological context. Although useful chemical methods have been developed for the synthesis of glycans, these typically require complex protection and deprotection steps along with challenging control of anomeric stereochemistry. Enzymatic methods offer an attractive alternative to chemical synthesis. In particular, the use of glycosynthases and thioglycoligases, classes of engineered glycoside hydrolases, offers an enticing approach to the stereo- and regioselective synthesis of glycans without the need for protecting groups. Herein, we describe recent progress in the use of glycosynthases and thioglycoligases for the synthesis of glycans and glycopolymers.

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Glycosylation of a Neoglycoprotein by Using Glycosynthase and Thioglycoligase Approaches: The Generation of a Thioglycoprotein

Cited by 39 publications

References 30 publications

Glycosidases in Carbohydrate Synthesis: When Organic Chemistry Falls Short

Glycosidases in Carbohydrate Synthesis: When Organic Chemistry Falls Short

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

Synthesis of Glycans and Glycopolymers Through Engineered Enzymes

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