In:
European Journal of Organic Chemistry, Wiley, Vol. 2020, No. 26 ( 2020-07-15), p. 3989-3996
Abstract:
Inhibitor protonation of azasugars of the isofagomine type when bound to enzyme can be investigated using photon induced electron transfer (PET) quenching of an attached fluorophore. For this purpose, Isofagomine, iso‐ d ‐ galacto ‐fagomine, and iso‐ l ‐ gulo ‐fagomine were converted to N ‐(10‐chloroanthracenenyl‐9‐alkyl) derivatives where the alkyl group contained one, two, or three methylene groups. The new derivatives displayed pH dependent fluorescence; as the ammonium forms they were fluorescent, while 90–99 % of the fluorescence was quenched in the amine forms. The 3 isofagomine derivatives were competitive inhibitors of T. Maritima Ι‐glucosidase with K i values from 0.37–4.6ΤM. Similarly, the iso‐ d ‐ galacto ‐fagomines inhibited A. Niger Ι‐galactosidase with K i values from 63–2000 n m . When bound to the enzymes the inhibitors displayed between 1–15 % fluorescence.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2020.26
DOI:
10.1002/ejoc.202000522
Language:
English
Publisher:
Wiley
Publication Date:
2020
detail.hit.zdb_id:
1475010-7
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