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Synthesis of 4-deoxy-4-thioarabinofuranosyl disaccharides, analogs of Mycobacterial arabinogalactan

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Title Synthesis of 4-deoxy-4-thioarabinofuranosyl disaccharides, analogs of Mycobacterial arabinogalactan
 
Creator Khare, Naveen K
Reynolds, Robert C
Maddry, Joseph A
 
Subject Tuberculosis
Glycosyl inhibitors
Mycobacterial arabinogalactan
Thiofuranoses thioarabinofuranosyl disaccharides
 
Description 1748-1752
The first chemical synthesis of disaccharides, octyl 5-O-(4-deoxy-4-thio-⍺-D-arabinofuranosyl)-⍺-D-arabinofuranoside 1 and octyl 5-O-(4-deoxy-4-thio-β-D-arabinofuranosyl)-⍺-D-arabinofuranoside 2 incorporating 4-deoxy-4-thioarabinose is described. Designed to mimic components of mycobacterial arabinogalactan, a major and essential constituent of the cell wall of tuberculosis and related bacteria, the compounds may disrupt cell wall biogenesis. A variety of coupling methods have been investigated before finding satisfactory techniques useful for thiofuranoses. Reductive deprotection of the sulfur-containing species is problematic, though lithium naphthalenide has proved to be an effective technique.
 
Date 2008-12-05T06:11:46Z
2008-12-05T06:11:46Z
2008-11
 
Type Article
 
Identifier 0376-4699
http://hdl.handle.net/123456789/2552
 
Language en_US
 
Publisher CSIR
 
Source IJCB Vol.47B(11) [November 2008]