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J. Biol. Chem., Vol. 265, Issue 12, 6734-6743, Apr, 1990
M Daffe, PJ Brennan and M McNeil
The peptidoglycan-bound arabinogalactan of a virulent strain of
Mycobacterium tuberculosis was per-O-methylated, partially hydrolyzed with
acid, and the resulting oligosaccharides reduced and O-pentadeute-
rioethylated. The per-O-alkylated oligoglycosyl alditol fragments were
separated by high pressure liquid chromatography and the structures of 43
of these constituents determined by 1H NMR and gas chromatography/mass
spectrometry. The arabinogalactan was shown to consist of a galactan
containing alternating 5-linked beta-D- galactofuranosyl (Galf) and
6-linked beta-D-Galf residues. The arabinan chains are attached to C-5 of
some of the 6-linked Galf residues. The arabinan is comprised of at least
three major structural domains. One is composed of linear 5-linked
alpha-D-arabinofuranosyl (Araf) residues; a second consists of branched
3,5-linked alpha-D-Araf units substituted with 5-linked alpha-D-Araf
residues at both branched positions. The non-reducing terminal region of
the arabinan was characterized by a 3,5-linked alpha-D-Araf residue
substituted at both branched positions with the disaccharide
beta-D-Araf-(1----2)-alpha-D- Araf. 13C NMR of intact soluble
arabinogalactan established the presence of both alpha- and beta-Araf
residues in this domain. This non- reducing terminal motif apparently
provides the structural basis of the dominant immunogenicity of
arabinogalactan within mycobacteria. A rhamnosyl residue occupies the
reducing terminus of the galactan core and may link the arabinogalactan to
the peptidoglycan. Evidence is also presented for the presence of minor
structural features involving terminal mannopyranosyl units. Models for
most of the heteropolysaccharide are proposed which should increase our
understanding of a molecule responsible for much of the immunogenicity,
pathogenicity, and peculiar physical properties of the mycobacterial cell.
Predominant structural features of the cell wall arabinogalactan of Mycobacterium tuberculosis as revealed through characterization of oligoglycosyl alditol fragments by gas chromatography/mass spectrometry and by 1H and 13C NMR analyses
Department of Microbiology, Colorado State University, Fort Collins 80523.
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