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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.47B [2008] >
IJC-B Vol.47B(11) [November 2008] >
| 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 |
| Source: | IJC-B Vol.47B(11) [November 2008]
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