Synthesis and Evaluation of Glycosyl Luciferins
Abstract: Measuring glycosidase activity is important to monitor any aberrations in carbohydrate hydrolase activity, but also for the screening of potential glycosidase inhibitors. To this end, synthetic substrates are needed which provide an enzyme‐dependent read‐out upon hydrolysis by the glycosidase. Herein, we present two new routes for the synthesis of caged luminescent carbohydrates, which can be used for determining glycosidase activity with a luminescent reporter molecule. The substrates were validated with glycosidase and revealed a clear linear range and enzyme‐dependent signal upon the in situ generation of the luciferin moiety from the corresponding nitrile precursors. Besides, we showed that these compounds could directly be synthesized from unprotected glycosyl‐α‐fluorides in a two‐step procedure with yields up to 75 %. The intermediate methyl imidate appeared a key intermediate which also reacted with d‐cysteine to give the corresponding d‐luciferin substrate rendering this a highly attractive method for synthesizing glycosyl luciferins in good yields.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Synthesis and Evaluation of Glycosyl Luciferins ; day:27 ; month:11 ; year:2023 ; extent:7
Chemistry - a European journal ; (27.11.2023) (gesamt 7)
- Creator
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Sondag, Daan
de Kleijne, Frank F. J.
Castermans, Sam
Chatzakis, Isa
van Geffen, Mark
van't Veer, Cornelis
van Heerde, Waander L.
Boltje, Thomas J.
Rutjes, Floris P. J. T.
- DOI
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10.1002/chem.202302547
- URN
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urn:nbn:de:101:1-2023112814462169061746
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 5:00 PM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Sondag, Daan
- de Kleijne, Frank F. J.
- Castermans, Sam
- Chatzakis, Isa
- van Geffen, Mark
- van't Veer, Cornelis
- van Heerde, Waander L.
- Boltje, Thomas J.
- Rutjes, Floris P. J. T.
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Stereoselective synthesis of C-glycosides with a glycosyl dianion
Synthesis of novel glycosyl 1,3,4-oxadiazole derivatives
Synthesis and AChE inhibitory activity of N -glycosyl benzofuran derivatives
N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors
Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
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Stereoselective synthesis of C-glycosides with a glycosyl dianion
Synthesis of novel glycosyl 1,3,4-oxadiazole derivatives
Synthesis and AChE inhibitory activity of N -glycosyl benzofuran derivatives
N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors
Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
Synthesis and bioactivity of novel C2-glycosyl oxadiazole derivatives as acetylcholinesterase inhibitors
Synthesis and bioactivity of novel C2-glycosyl triazole derivatives as acetylcholinesterase inhibitors
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