The Structural Basis of Glycosidase Inhibition by Five-Membered Iminocyclitols: The Clan A Glycoside Hydrolase Endoglycoceramidase as a Model System

M.E.C. Caines; S.M. Hancock; C.A. Tarling; T.M. Wrodnigg; Robert Stick; A.E. Stutz; A. Vasella; S.G. Withers; N.C.J. Strynadka

doi:10.1002/anie.200700268

The Structural Basis of Glycosidase Inhibition by Five-Membered Iminocyclitols: The Clan A Glycoside Hydrolase Endoglycoceramidase as a Model System

M.E.C. Caines, S.M. Hancock, C.A. Tarling, T.M. Wrodnigg, Robert Stick, A.E. Stutz, A. Vasella, S.G. Withers, N.C.J. Strynadka

School of Molecular Sciences

Research output: Contribution to journal › Article

36 Citations (Scopus)

Abstract

Fitting five into six: The crystal structure of a glycosidase-bound, five-membered iminocyclitol inhibitor was determined (see picture), and its binding interactions were compared to those of the classical six-membered iminocyclitol inhibitors isofagomine and glucoimidazole and of the glycosyl–enzyme intermediate. This information may be used to develop more potent and specific therapeutically useful glycosidase inhibitors.

Original language	English
Pages (from-to)	4474-4476
Journal	Angewandte Chemie (International Edition)
Volume	46
Issue number	24
DOIs	https://doi.org/10.1002/anie.200700268
Publication status	Published - 2007

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Caines, M. E. C., Hancock, S. M., Tarling, C. A., Wrodnigg, T. M., Stick, R., Stutz, A. E., Vasella, A., Withers, S. G., & Strynadka, N. C. J. (2007). The Structural Basis of Glycosidase Inhibition by Five-Membered Iminocyclitols: The Clan A Glycoside Hydrolase Endoglycoceramidase as a Model System. Angewandte Chemie (International Edition), 46(24), 4474-4476. https://doi.org/10.1002/anie.200700268

Caines, M.E.C. ; Hancock, S.M. ; Tarling, C.A. ; Wrodnigg, T.M. ; Stick, Robert ; Stutz, A.E. ; Vasella, A. ; Withers, S.G. ; Strynadka, N.C.J. / The Structural Basis of Glycosidase Inhibition by Five-Membered Iminocyclitols: The Clan A Glycoside Hydrolase Endoglycoceramidase as a Model System. In: Angewandte Chemie (International Edition). 2007 ; Vol. 46, No. 24. pp. 4474-4476.

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abstract = "Fitting five into six: The crystal structure of a glycosidase-bound, five-membered iminocyclitol inhibitor was determined (see picture), and its binding interactions were compared to those of the classical six-membered iminocyclitol inhibitors isofagomine and glucoimidazole and of the glycosyl–enzyme intermediate. This information may be used to develop more potent and specific therapeutically useful glycosidase inhibitors.",

author = "M.E.C. Caines and S.M. Hancock and C.A. Tarling and T.M. Wrodnigg and Robert Stick and A.E. Stutz and A. Vasella and S.G. Withers and N.C.J. Strynadka",

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Caines, MEC, Hancock, SM, Tarling, CA, Wrodnigg, TM, Stick, R, Stutz, AE, Vasella, A, Withers, SG & Strynadka, NCJ 2007, 'The Structural Basis of Glycosidase Inhibition by Five-Membered Iminocyclitols: The Clan A Glycoside Hydrolase Endoglycoceramidase as a Model System', Angewandte Chemie (International Edition), vol. 46, no. 24, pp. 4474-4476. https://doi.org/10.1002/anie.200700268

The Structural Basis of Glycosidase Inhibition by Five-Membered Iminocyclitols: The Clan A Glycoside Hydrolase Endoglycoceramidase as a Model System. / Caines, M.E.C.; Hancock, S.M.; Tarling, C.A.; Wrodnigg, T.M.; Stick, Robert; Stutz, A.E.; Vasella, A.; Withers, S.G.; Strynadka, N.C.J.

In: Angewandte Chemie (International Edition), Vol. 46, No. 24, 2007, p. 4474-4476.

Research output: Contribution to journal › Article

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