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  • Title: Anomer-selective glycosidase inhibition by 2-N-alkylated 1-azafagomines.
    Author: Lopez Lopez O, Bols M.
    Journal: Chembiochem; 2007 Apr 16; 8(6):657-61. PubMed ID: 17352429.
    Abstract:
    Alkylation of 1-azafagomine at the 2-N position was achieved by reductive amination of 1-N-acetyl-3,4,6-tri-O-benzyl-1-azafagomine by using aldehydes, palladium hydroxide, and hydrogen in EtOAc/water/acetic acid followed by deprotection. The 2-N-butyl, hexyl, heptyl, nonyl, decyl, and 3-phenylpropyl derivatives were made in this manner, and were tested for inhibition of alpha-glucosidase from yeast, and of beta-glucosidase from almonds. The new compounds were stronger beta-glucosidase inhibitors than 1-azafagomine, but weaker alpha-glucosidase inhibitors.
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