The structural basis of glycosidase inhibition by five-membered iminocyclitols:: The clan a glycoside hydrolase endoglycoceramidase as a model system

被引:36
作者
Caines, Matthew E. C.
Hancock, Susan M.
Tarling, Chris A.
Wrodnigg, Tanja M.
Stick, Robert V.
Stuetz, Arnold E.
Vasella, Andrea
Withers, Stephen G.
Strynadka, Natalie C. J.
机构
[1] Univ British Columbia, Dept Biochem & Mol Biol, Vancouver, BC V6T 1Z3, Canada
[2] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z3, Canada
[3] Graz Univ Technol, Inst Organ Chem, A-8010 Graz, Austria
[4] Univ Western Australia, Sch Biomed Biomol & Chem Sci, Crawley, WA 6009, Australia
[5] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
carbohydrates; drug design; glycosidases; iminocyclitols; inhibitors;
D O I
10.1002/anie.200700268
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Fitting five into six: The crystal structure of a glycosidase-bound, flve-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. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4474 / 4476
页数:3
相关论文
共 28 条
[11]  
GOSS PE, 1994, CANCER RES, V54, P1450
[12]   INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE [J].
GRUTERS, RA ;
NEEFJES, JJ ;
TERSMETTE, M ;
DEGOEDE, REY ;
TULP, A ;
HUISMAN, HG ;
MIEDEMA, F ;
PLOEGH, HL .
NATURE, 1987, 330 (6143) :74-77
[13]  
ITO M, 1986, J BIOL CHEM, V261, P14278
[14]   Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: New structures for antivirals and osteoarthritis [J].
Liang, PH ;
Cheng, WC ;
Lee, YL ;
Yu, HP ;
Wu, YT ;
Lin, YL ;
Wong, CH .
CHEMBIOCHEM, 2006, 7 (01) :165-173
[15]   Efficient asymmetric synthesis of an azasugar in water [J].
Lindström, UM ;
Ding, R ;
Hidestål, O .
CHEMICAL COMMUNICATIONS, 2005, (13) :1773-1774
[16]   Synthesis with glycosynthases: Cello-oligomers of isofagomine and a tetrahydrooxazine as cellulase inhibitors [J].
Macdonald, JM ;
Stick, RV ;
Tilbrook, DMG ;
Withers, SG .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2002, 55 (12) :747-752
[17]   Inhibition of hepatitis B virus DNA replication by imino sugars without the inhibition of the DNA polymerase:: Therapeutic implications [J].
Mehta, A ;
Carrouée, S ;
Conyers, B ;
Jordan, R ;
Butters, T ;
Dwek, RA ;
Block, TM .
HEPATOLOGY, 2001, 33 (06) :1488-1495
[18]   exo-imino to endo-iminocyclitol rearrangement.: A general route to five-membered antiviral azasugars [J].
Moriarty, Robert M. ;
Mitan, Carmen I. ;
Branza-Nichita, Norica ;
Phares, Kenneth R. ;
Parrish, Damon .
ORGANIC LETTERS, 2006, 8 (16) :3465-3467
[19]   Combinatorial library of five-membered iminocyclitol and the inhibitory activities against glyco-enzymes [J].
Saotome, C ;
Wong, CH ;
Kanie, O .
CHEMISTRY & BIOLOGY, 2001, 8 (11) :1061-1070
[20]   A versatile synthetic strategy for the preparation and discovery of new iminocyclitols as inhibitors of glycosidases [J].
Takebayashi, M ;
Hiranuma, S ;
Kanie, Y ;
Kajimoto, T ;
Kanie, O ;
Wong, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5280-5291