ArticleBeilstein journal of organic chemistry2019
Cyclopropene derivatives of aminosugars for metabolic glycoengineering.
Article in Beilstein journal of organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 19 citations in OpenAlex.
- Metabolic Glycan Labeling of Cancer Cells Using Variably Acetylated Monosaccharides.Bioconjugate chemistry · 2022Article
- An Advanced 'clickECM' That Can be Modified by the Inverse-Electron-Demand Diels-Alder Reaction.Chembiochem : a European journal of chemical biology · 2022Article
- Metabolic Glycoengineering with Azide- and Alkene-Modified Hexosamines: Quantification of Sialic Acid Levels.Chembiochem : a European journal of chemical biology · 2021Article
- Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering.Frontiers in chemistry · 2021Review
- Exploiting metabolic glycoengineering to advance healthcare.Nature reviews. Chemistry · 2019Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Cyclopropenes have been proven valuable chemical reporter groups for metabolic glycoengineering (MGE). They readily react with tetrazines in an inverse electron-demand Diels-Alder (DAinv) reaction, a prime example of a bioorthogonal ligation reaction, allowing their visualization in biological systems. Here, we present a comparative study of six cyclopropene-modified hexosamine derivatives and their suitability for MGE. Three mannosamine derivatives in which the cyclopropene moiety is attached to the sugar by either an amide or a carbamate linkage and that differ by the presence or absence of a stabilizing methyl group at the double bond have been examined. We determined their DAinv reaction kinetics and their labeling intensities after metabolic incorporation. To determine the efficiencies by which the derivatives are metabolized to sialic acids, we synthesized and investigated the corresponding cyclopropane derivatives because cyclopropenes are not stable under the analysis conditions. From these experiments, it became obvious that
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