Glycosidase inhibition by ring-modified castanospermine analogues: tackling enzyme selectivity by inhibitor tailoring

被引：48

作者：

Aguilar-Moncayo, Matilde ^{[2
]}

Gloster, Tracey M. ^{[1
]}

Turkenburg, Johan P. ^{[1
]}

Isabel Garcia-Moreno, M. ^{[2
]}

Ortiz Mellet, Carmen ^{[2
]}

Davies, Gideon J. ^{[1
]}

Garcia Fernandez, Jose M. ^{[3
]}

机构：

[1] Univ York, Dept Chem, York Struct Biol Lab, York YO10 5YW, N Yorkshire, England

[2] Univ Seville, Fac Quim, Dept Quim Organ, Seville 41012, Spain

[3] Univ Seville, CSIC, Inst Invest Quim, Seville 41092, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 13期

关键词：

TRANSITION-STATE; BIOLOGICAL EVALUATION; BETA-GLUCOSIDASE; GLYCOGEN-PHOSPHORYLASE; CYCLODEXTRIN ANALOGS; MOLECULAR-BASIS; HIGHLY POTENT; BINDING; GLYCOMIMETICS; ISOFAGOMINE;

D O I：

10.1039/b906968b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of a panel of iso(thio)urea-type ring-modified castanospermine analogues bearing a freely mutarotating pseudoanomeric hydroxyl group results in tight-binding beta-glucosidase inhibitors with unusual binding signatures; the presence of an N-octyl substituent imparts a remarkable anomeric selectivity, promoting strong binding of the appropriate beta-anomer by the beta-glucosidase.

引用

页码：2738 / 2747

页数：10

共 59 条

[1] Molecular Basis for β-Glucosidase Inhibition by Ring-Modified Calystegine Analogues [J].

Aguilar, Matilde ;

Gloster, Tracey M. ;

Garcia-Moreno, M. Isabel ;

Mellet, Carmen Ortiz ;

Davies, Gideon J. ;

Llebaria, Amadeu ;

Casas, Josefina ;

Egido-Gabas, Meritxell ;

Fernandez, Jose M. Garcia .

CHEMBIOCHEM, 2008, 9 (16) :2612-2618

[2] Synthesis and biological evaluation of guanidine-type iminosugars [J].

Aguilar, Matilde ;

Diaz-Perez, Paula ;

Isabel Garcia-Moreno, M. ;

Ortiz Mellet, Carmen ;

Garcia Fernandez, Jose M. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1995-1998

[3]

[Anonymous], 2007, IMINOSUGARS SYNTHESI

[4] Glycosidase inhibitors: update and perspectives on practical use [J].

Asano, N .

GLYCOBIOLOGY, 2003, 13 (10) :93R-104R

[5] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[6] THE CCP4 SUITE - PROGRAMS FOR PROTEIN CRYSTALLOGRAPHY [J].

BAILEY, S .

ACTA CRYSTALLOGRAPHICA SECTION D-BIOLOGICAL CRYSTALLOGRAPHY, 1994, 50 :760-763

[7]

Blanco JLJ, 1997, CHEM COMMUN, P1969

[8] Urea-, thiourea-, and guanidine-linked glycooligomers as phosphate binders in water [J].

Blanco, Jose L. Jimenez ;

Bootello, Purificacion ;

Benito, Juan M. ;

Mellet, Carmen Ortiz ;

Fernandez, Jose M. Garcia .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5136-5143

[9] A CONFORMATIONAL STUDY OF HYDROXYMETHYL GROUPS IN CARBOHYDRATES INVESTIGATED BY H-1-NMR SPECTROSCOPY [J].

BOCK, K ;

DUUS, JO .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (04) :513-543

[10] A large difference in the thermodynamics of binding of isofagomine and 1-deosynojirimycin to β-glucosidase [J].

Bülow, A ;

Plesner, IW ;

Bols, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (35) :8567-8568

← 1 2 3 4 5 6 →