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Anomer‐Selective Glycosidase Inhibition by 2‐ N ‐Alkylated 1‐Azafagomines
Author(s) -
Lopez Lopez Oscar,
Bols Mikael
Publication year - 2007
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200700012
Subject(s) - alkylation , chemistry , reductive amination , acetic acid , amination , yeast , anomer , organic chemistry , stereochemistry , medicinal chemistry , catalysis , biochemistry
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 α‐glucosidase from yeast, and of β‐glucosidase from almonds. The new compounds were stronger β‐glucosidase inhibitors than 1‐azafagomine, but weaker α‐glucosidase inhibitors.