Research output: Contribution to journal › Article
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Journal | Organic Letters |
---|---|
Date | Accepted/In press - 14 Nov 2018 |
Date | E-pub ahead of print - 14 Nov 2018 |
Date | Published (current) - 7 Dec 2018 |
Issue number | 23 |
Volume | 20 |
Number of pages | 5 |
Pages (from-to) | 7488-7492 |
Early online date | 14/11/18 |
Original language | English |
Understanding the enzyme reaction mechanism can lead to the design of enzyme inhibitors. A Claisen rearrangement was used to allow conversion of an α-1,4-disaccharide into an α-1,3-linked glycosyl carbasugar to target the endo-α-mannosidase from the GH99 glycosidase family, which, unusually, is believed to act through a 1,2-anhydrosugar "epoxide" intermediate. Using NMR and X-ray crystallography, it is shown that glucosyl carbasugar α-aziridines can act as reasonably potent endo-α-mannosidase inhibitors, likely by virtue of their shape mimicry and the interactions of the aziridine nitrogen with the conserved catalytic acid/base of the enzyme active site.
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Project: Research project (funded) › Research
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