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Title: Synthesis of 4-deoxy-4-thioarabinofuranosyl disaccharides, analogs of Mycobacterial arabinogalactan
Authors: Khare, Naveen K
Reynolds, Robert C
Maddry, Joseph A
Keywords: Tuberculosis;Glycosyl inhibitors;Mycobacterial arabinogalactan;Thiofuranoses thioarabinofuranosyl disaccharides
Issue Date: Nov-2008
Publisher: CSIR
Abstract: 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.
Page(s): 1748-1752
ISSN: 0376-4699
Appears in Collections:IJC-B Vol.47B(11) [November 2008]

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