Potent Fluoro-oligosaccharide Probes of Adhesion in Toxoplasmosis

被引：58

作者：

Allman, Sarah A. ^{[5
]}

Jensen, Henrik H. ^{[5
]}

Vijayakrishnan, Balakumar ^{[5
]}

Garnett, James A. ^{[1
]}

Leon, Ester ^{[1
]}

Liu, Yan ^{[2
]}

Anthony, Daniel C. ^{[3
]}

Sibson, Nicola R. ^{[4
]}

Feizi, Ten ^{[2
]}

Matthews, Stephen ^{[1
]}

Davis, Benjamin G. ^{[5
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, London SW7 2AY, England

[2] Imperial Coll London, Glycosci Lab, Fac Med, Harrow HA1 3GX, Middx, England

[3] Univ Oxford, Dept Pharmacol, Oxford OX1 3QT, England

[4] Univ Oxford, Churchill Hosp, CRUK MRC Gray Inst Radiat Oncol & Biol, Oxford OX3 7LJ, England

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

来源：

CHEMBIOCHEM | 2009年 / 10卷 / 15期

基金：

英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;

关键词：

fluorine; fluorosugars; lectins; oligosaccharides; toxoplasmosis; LECTIN-CHAPERONE CALRETICULIN; CRUZI TRANS-SIALIDASE; HOST-CELL SURFACE; TRYPANOSOMA-CRUZI; REGIOSELECTIVE GLYCOSYLATION; HYDROGEN-BONDS; GLYCOGEN-PHOSPHORYLASE; MICRONEMAL PROTEINS; N-ACETYLGLUCOSAMINE; CRYSTAL-STRUCTURE;

D O I：

10.1002/cbic.200900425

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：

Unnatural, NMR- and MRI-active fluorinated sugar probes, del signed and synthesised to bind to the pathogenic protein TgMIC1 from Toxoplasma gondii, were found to display binding potency equal to and above that of the natural ligand. Dissection of the binding mechanism and modes, including the first X-ray crystal structures of a fluoro-oligosaccharide bound to a lectin, demonstrate that it is possible to create effective fluorinated probe ligands for the study of, and perhaps intervention in, sugar-protein binding events.

引用

页码：2522 / 2529

页数：8

共 68 条

[1] A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives [J].

Albert, M ;

Dax, K ;

Ortner, J .

TETRAHEDRON, 1998, 54 (19) :4839-4848

[2]

Albert M, 1999, SYNLETT, P1483

[3] Targeted glycosyl donor delivery for site-selective glycosylation [J].

Anilkumar, G ;

Nair, LG ;

Fraser-Reid, B .

ORGANIC LETTERS, 2000, 2 (17) :2587-2589

[4] Towards the preparation of 2"-deoxy-2"-fluoro-adenophostin A. Study of the glycosylation reaction [J].

Benito, David ;

Matheu, M. Isabel ;

Morere, Alain ;

Diaz, Yolanda ;

Castillon, Sergio .

TETRAHEDRON, 2008, 64 (48) :10906-10911

[5] Donor substrate binding to trans-sialidase of Trypanosoma cruzi as studied by STD NMR [J].

Blume, Astrid ;

Neubacher, Bjoern ;

Thiem, Joachim ;

Peters, Thomas .

CARBOHYDRATE RESEARCH, 2007, 342 (12-13) :1904-1909

[6] Atomic resolution insight into host cell recognition by Toxoplasma gondii [J].

Blumenschein, Tharin M. A. ;

Friedrich, Nikolas ;

Childs, Robert A. ;

Saouros, Savvas ;

Carpenter, Elisabeth P. ;

Campanero-Rhodes, Maria A. ;

Simpson, Peter ;

Chai, Wengang ;

Koutroukides, Theodoros ;

Blackman, Michael J. ;

Feizi, Ten ;

Soldati-Favre, Dominique ;

Matthews, Stephen .

EMBO JOURNAL, 2007, 26 (11) :2808-2820

[7]

Boons GJ, 1997, SYNLETT, P809

[8]

BORDERS CL, 1994, PROTEIN SCI, V3, P541

[9] A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor [J].

Burkart, MD ;

Zhang, ZY ;

Hung, SC ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11743-11746

[10] The crystal structure and mode of action of trans-sialidase, a key enzyme in Trypanosoma cruzi pathogenesis [J].

Buschiazzo, A ;

Amaya, MF ;

Cremona, ML ;

Frasch, AC ;

Alzari, PM .

MOLECULAR CELL, 2002, 10 (04) :757-768

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