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6‐Amino‐6‐deoxy‐5,6‐di‐ N ‐( N ′‐octyliminomethylidene)nojirimycin: Synthesis, Biological Evaluation, and Crystal Structure in Complex with Acid β‐Glucosidase
Author(s) -
Brumshtein Boris,
AguilarMoncayo Matilde,
GarcíaMoreno M. Isabel,
Ortiz Mellet Carmen,
García Fernández José M.,
Silman Israel,
Shaaltiel Yoseph,
Aviezer David,
Sussman Joel L.,
Futerman Anthony H.
Publication year - 2009
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.200900142
Subject(s) - anomer , stereochemistry , glucosidases , enzyme , chemistry , amino acid residue , amino acid , absolute configuration , biochemistry , peptide sequence , gene
Abstract 6‐Amino‐6‐deoxy‐5,6‐di‐ N ‐( N ′‐octyliminomethylidene)nojirimycin , a reducing analogue of N ‐nonyl‐1‐deoxynojirimycin, proved to be a potent and very selective inhibitor of β‐glucosidases, including human acid β‐glucosidase. Structural studies of the enzyme–inhibitor complex showed a binding mode in which the anomeric hydroxy group is accommodated in the “wrong” α configuration.