Identification of the 5-methylthiopentosyl substituent in mycobacterium tuberculosis lipoarabinomannan

被引：46

作者：

Turnbull, WB

Shimizu, KH

Chatterjee, D

Homans, SW

Treumann, A

机构：

[1] Colorado State Univ, Dept Microbiol Immunol & Pathol, Ft Collins, CO 80523 USA

[2] Univ Leeds, Sch Biochem & Microbiol, Astbury Ctr Struct Mol Biol, Leeds LS2 9JT, W Yorkshire, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 30期

关键词：

carbohydrates; cell wall; NMR spectroscopy; structure elucidation; xylofuranose;

D O I：

10.1002/anie.200454119

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unexpected configuration of a novel carbohydrate structure in the cell wall of Mycobacterium tuberculosis was revealed by synthesizing the isomers of 5-deoxy-5-methylthio-D-pentofuranose as α- and β-methyl glycosides, and analyzing their NMR spectra (see picture). Cell-wall glycolipids are crucial factors for the pathogenesis of infectious diseases, and the results presented might open new research avenues into host-pathogen interactions.

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收藏

页码：3918 / 3922

页数：5

相关论文

共 23 条

[1] COMPLEXES OF CARBOHYDRATES WITH METAL CATIONS .5. SYNTHESES OF METHYL GLYCOSIDES IN PRESENCE OF METAL-IONS [J].

ANGYAL, SJ ;

BODKIN, CL ;

PARRISH, FW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (07) :1541-1549

[2] CHROMATOGRAPHIC SEPARATION OF ANOMERIC GLYCOSIDES .2. NEW CRYSTALLINE METHYLFURANOSIDES OF GALACTOSE, ARABINOSE AND XYLOSE [J].

AUGESTAD, I ;

BERNER, E .

ACTA CHEMICA SCANDINAVICA, 1954, 8 (02) :251-256

[3] Bicyclic azasugars containing a glycosidic heteroatom 2: D-lyxose analogues [J].

Berges, DA ;

Zhang, N ;

Hong, LW .

TETRAHEDRON, 1999, 55 (50) :14251-14260

[4] GLYCOSIDATION OF SUGARS .2. METHANOLYSIS OF D-XYLOSE, D-ARABINOSE, D-LYXOSE, AND D-RIBOSE [J].

BISHOP, CT ;

COOPER, FP .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1963, 41 (11) :2743-&

[5] Mycobacterial lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects [J].

Chatterjee, D ;

Khoo, KH .

GLYCOBIOLOGY, 1998, 8 (02) :113-120

[6]

Chopra P, 2003, INDIAN J MED RES, V117, P1

[7] A NATURALLY-OCCURRING ANALOG OF METHYLTHIOADENOSINE (MTA) FROM THE NUDIBRANCH MOLLUSK DORIS-VERRUCOSA [J].

CIMINO, G ;

CRISPINO, A ;

DESTEFANO, S ;

GAVAGNIN, M ;

SODANO, G .

EXPERIENTIA, 1986, 42 (11-12) :1301-1302

[8]

FERRIER RJ, 1984, J CHEM SOC P1, V8, P1689

[9] Lipomannan and lipoarabinomannan from a clinical isolate of Mycobacterium kansasii -: Novel structural features and apoptosis-inducing properties [J].

Guérardel, Y ;

Maes, E ;

Briken, V ;

Chirat, F ;

Leroy, Y ;

Locht, C ;

Strecker, G ;

Kremer, L .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (38) :36637-36651

[10] STARFISH SAPONINS .45. NOVEL SULFATED STEROIDAL GLYCOSIDES FROM THE STARFISH ASTROPECTEN-SCOPARIUS [J].

IORIZZI, M ;

MINALE, L ;

RICCIO, R ;

KAMIYA, H .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (05) :1225-1233