6‐Amino‐6‐deoxy‐5,6‐di‐ N ‐( N ′‐octyliminomethylidene)nojirimycin: Synthesis, Biological Evaluation, and Crystal Structure in Complex with Acid β‐Glucosidase | Zendy

Brumshtein Boris | Zendy; AguilarMoncayo Matilde | Zendy; GarcíaMoreno M. Isabel | Zendy; Ortiz Mellet Carmen | Zendy; García Fernández José M. | Zendy; Silman Israel | Zendy; Shaaltiel Yoseph | Zendy; Aviezer David | Zendy; Sussman Joel L. | Zendy; Futerman Anthony H. | Zendy

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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

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.

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