NDLI: Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan

Content Provider	Royal Society of Chemistry (RSC)
Author	Gandolfi-Donadío, Lucía Lederkremer, Rosa M. de Gallo-Rodriguez, Carola Santos, Malena
Copyright Year	2011
Abstract	Mycolyl-arabinogalactan (mAG) complex is a major component of the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis disease. Due to the essentiality of the cell wall for mycobacterium viability, knowledge of the biosynthesis of the arabinogalactan is crucial for the development of new therapeutic agents. In this context, we have synthesized two new branched arabinogalactafuranose tetrasaccharides, decenyl β-D-Galf-(1→5)-β-D-Galf-(1→6)[α-D-Araf(1→5)]-β-D-Galf (1) and decenyl β-D-Galf-(1→6)-[α-D-Araf-(1→5)]-β-D-Galf-(1→5)-β-D-Galf (2), as interesting tools for arabinofuranosyl transferase studies. The aldonolactone strategy for the introduction of the internal D-Galf was employed, allowing the construction of oligosaccharides from the non-reducing to the reducing end. Moreover, a one-pot procedure was developed for the synthesis of trisaccharide lactone 21, precursor of 2, which involved a glycosylation-deprotection-glycosylation sequence, through the use of TMSOTf as catalyst of the trichloroacetimidate method as well as promoter of TBDMS deprotection.
Starting Page	2085
Ending Page	2097
Page Count	13
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	7
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c0ob00989j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Mycobacterium Mycobacterium tuberculosis Transferase Trimethylsilyl trifluoromethanesulfonate Lactone Arabinogalactan Silyl ether Cell wall Trisaccharide
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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