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Communication: Synthesis of Me α-L-Rhap-(1↠3)-2-O-Me-α-L-Rhap And Me 2,3,4-Tri-O-Me-α-L-Fucp-(1↠3)-α-L-Rhap-(1↠3)-2-O-Me-α-L-Rhap : Oligosaccha-Ride Segments of Phenolic Glycolipids inMycobacterium Bovis BcgandTuberculosis Strain Canetti

 

作者: Mukund K Gurjar,   G Viswanadham,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1991)
卷期: Volume 10, issue 3  

页码: 481-485

 

ISSN:0732-8303

 

年代: 1991

 

DOI:10.1080/07328309108543923

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

The revived interest in phenolic glycolipids of pathogenic mycobacteria is evoked by a widespread1-3use ofMycobacterium (M.) lepraespecific antigen for serodiagnosis of leprosy patients. As a consequence, a few phenolic glycolipids of other mycobacterias were isolated and structurally elucidated. Recently Vercellone and Puzo4reported the isolation of new phenolic glycolipids not yet described inM. bovisBCG. The combination of sugars in one of the glycolipids was identified as 3-O-(α-L-rhamnopyranosyl)-2-O-methyl-α-L-rhamnopyranoside (1) which is closely related to the trisaccharide segment (2) ofM. tuberculosisstrain Canetti.5The latter contains 2,3,4-tri-O-methyl-L-fucopyranosyl monosaccharide α-linked to 3′ position of 1. It has been emphasised that new found glycolipids ofM. bovisBCG could share common epitopes with those ofM. tuberculosis, thus leading to false positive immunoabsorbent assay tests during screening of tuberculosis patients. In addition, there is concern regarding the involvement of one of the new found glycolipids in the stimulation of T suppressor cells, thus adding to the conflicting results noted in the protection ofM. tuberculosisbyM. bovisBCG. In essence the new found phenolic glycolipids ofM. bovisBCG are associated with interesting but unclear biological profiles. We now report the synthesis of these closely related oligosaccharides, 1 (R = Me) and 2 (R = Me).

 

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