AI Article Synopsis
- - The study focuses on creating and testing three types of fluorescent N-alkyl cyclophellitol aziridine probes to study specific enzymes: β-glucosidase (GBA), α-galactosidase (GLA), and α-fucosidase (FUCA).
- - These N-alkyl aziridine probes are easier to synthesize and more stable in various conditions compared to previously developed acyl aziridine probes, making them more user-friendly.
- - The N-alkyl variant effectively labels GBA, similar to its N-acyl equivalent, while N-acyl probes perform better for GLA and FUCA, suggesting that both probe types should be used in future enzyme studies.
Article Abstract
The synthesis and evaluation as activity-based probes (ABPs) of three configurationally distinct, fluorescent N-alkyl cyclophellitol aziridine isosteres for profiling GH1 β-glucosidase (GBA), GH27 α-galactosidase (GLA) and GH29 α-fucosidase (FUCA) is described. In comparison with the corresponding acyl aziridine ABPs reported previously, the alkyl aziridine ABPs are synthesized easily and are more stable in mild acidic and basic media, and are thus easier to handle. The β-glucose-configured alkyl aziridine ABP proves equally effective in labeling GBA as its N-acyl counterpart, whereas the N-acyl aziridines targeting GLA and FUCA outperform their N-alkyl counterparts. Alkyl aziridines can therefore be an attractive alternative in retaining glycosidase ABP design, but in targeting a new retaining glycosidase both N-alkyl and N-acyl aziridines are best considered at the onset of a new study.
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| http://dx.doi.org/10.1002/chem.201501313 | DOI Listing |
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