Looking glass inhibitors:: efficient synthesis and biological evaluation of D-deoxyfuconojirimycin

被引：33

作者：

Blériot, Y

Gretzke, D

Krülle, TM

Butters, TD

Dwek, RA

Nash, RJ

Asano, N

Fleet, GWJ

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Oxford, Dept Biochem, Glycobiol Inst, Oxford OX1 3QU, England

[3] IGER, Mol Nat Ltd, Aberystwyth SY23 3EB, Ceredigion, Wales

[4] Hakuriku Univ, Dept Biochem, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201181, Japan

来源：

CARBOHYDRATE RESEARCH | 2005年 / 340卷 / 18期

关键词：

galactostatin; glycosidase inhibitor; 1-deoxyfuconojirimycin; iminosugar; mirror image;

D O I：

10.1016/j.carres.2005.10.002

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

1, 6-Dideoxygalactostatin, the mirror image of 1-deoxy-L-fuconojirimycin, was efficiently prepared from 2,3-Ow-isopropylidene-L-lyxonolactone in four steps and evaluated as a glycosidase inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2713 / 2718

页数：6

共 40 条

[1] Recent advances in the chemistry of azapyranose sugars [J].

Afarinkia, K ;

Bahar, A .

TETRAHEDRON-ASYMMETRY, 2005, 16 (07) :1239-1287

[2] Small-molecule therapeutics for the treatment of glycolipid lysosomal storage disorders [J].

Butters, TD ;

Mellor, HR ;

Narita, K ;

Dwek, RA ;

Platt, FM .

PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY B-BIOLOGICAL SCIENCES, 2003, 358 (1433) :927-945

[3] Therapeutic applications of imino sugars in lysosomal storage disorders [J].

Butters, TD ;

Dwek, RA ;

Platt, FM .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2003, 3 (05) :561-574

[4] 6-deoxy-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series, D-fuco-nojirimycin and their 1-deoxyderivatives via hetero-Diels-Alder cycloadditions. [J].

Defoin, A ;

Sarazin, H ;

Streith, J .

TETRAHEDRON, 1997, 53 (40) :13783-13796

[5]

DEFOIN A, 1995, SYNLETT, P1187

[6] Targeting glycosylation as a therapeutic approach [J].

Dwek, RA ;

Butters, TD ;

Platt, FM ;

Zitzmann, N .

NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (01) :65-75

[7] SYNTHESIS FROM D-GLUCOSE OF 1,5-DIDEOXY-1,5-IMINO-L-FUCITOL, A POTENT ALPHA-L-FUCOSIDASE INHIBITOR [J].

FLEET, GWJ ;

SHAW, AN ;

EVANS, SV ;

EVANS, SV .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (13) :841-842

[8] DELTA-LACTAMS - SYNTHESIS FROM D-GLUCOSE, AND PRELIMINARY EVALUATION AS A FUCOSIDASE INHIBITOR, OF L-FUCONIC-DELTA-LACTAM [J].

FLEET, GWJ ;

RAMSDEN, NG ;

DWEK, RA ;

RADEMACHER, TW ;

FELLOWS, LE ;

NASH, RJ ;

GREEN, DS ;

WINCHESTER, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (07) :483-485

[9] PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND MANNONOLACTAM FROM L-GULONOLACTONE - SYNTHESIS OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE [J].

FLEET, GWJ ;

RAMSDEN, NG ;

WITTY, DR .

TETRAHEDRON, 1989, 45 (01) :319-326

[10]

FLEET GWJ, 1989, J CHEM SOC P1, P65

← 1 2 3 4 →