Chemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.

@article{Marinoalbernas1988ChemicalSO,
  title={Chemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.},
  author={J. R. Marino-albernas and vicente Verez-Bencomo and L L Gonz{\'a}lez-Rodr{\'i}guez and Carlos P{\'e}rez-Mart{\'i}nez and E Gonzalez-Abreu Castell and A Gonz{\'a}lez-Segredo},
  journal={Carbohydrate research},
  year={1988},
  volume={183 2},
  pages={
          175-82
        }
}
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19 Citations

19 Citations

A new approach to the chemical synthesis of the trisaccharide, and the terminal di- and mono-saccharide units of the major, serologically active glycolipid from Mycobacterium leprae.
An n.m.r. and conformational analysis of the terminal trisaccharide from the serologically active glycolipid of Mycobacterium leprae in different solvents.
Regioselective syntheses of trehalose-containing trisaccharides using various glycohydrolases.
Synthesis of carbohydrate-amino acid conjugates related to the capsular antigen K54 from Escherichia coli O6:K54:H10 and artificial antigens therefrom.
Synthesis of methyl 2,4-di-O-methyl-3-O-(2-O-methyl-α-l-rhamnopyranosyl)-α-l-rhamnopyranoside and methyl 2,4-di-O-methyl-3-O-[2-O-methyl-3-O-(2-O-methyl-α-l-fucopyranosyl)-α-l-rhamnopyranosyl]-α-l- rhamnopyranoside: di- and tri-saccharide segments of a phenolic glycolipid of Mycobacterium kansasii
Communication: Synthesis of Me α-L-Rhap-(1↠3)-2-O-Me-α-L-Rhap And Me 2,3,4-Tri-O-Me-α-L-Fucp-(1↠3)-α-L-Rhap-(1↠3)-2-O-Me-α-L-Rhap : Oligosaccha-Ride Segments of Phenolic Glycolipids in Mycobacterium Bovis Bcg and Tuberculosis Strain Canetti
TLDR
It has been emphasised that new found glycolipids of M. bovis BCG could share common epitopes with those ofM.
Asymmetric synthesis of methyl 6-deoxy-3-O-methyl-alpha-L-mannopyranoside from a non-carbohydrate precursor.
The variable surface glycolipids of mycobacteria: structures, synthesis of epitopes, and biological properties.
A stereoconvergent synthesis of the oligosaccharide segment of glyco- peptidolipid antigen of mycobacterium avium serotype 4 : a dominant serovariant observed in patients with acquired immune deficiency syndrome
The carbohydrate- and lipid-containing cell wall of mycobacteria, phenolic glycolipids: structure and immunological properties.
  • G. Puzo
  • Biology, Chemistry
    Critical reviews in microbiology
  • 1990
TLDR
The search of immunoreactive glycolipids and their function analysis remain a challenge for chemists and immunologists for the understanding of the mycobacteria pathogenicity.
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References

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Chemical synthesis of the trisaccharide unit of the species-specific phenolic glycolipid from Mycobacterium leprae.
Use of an artificial antigen containing the 3,6-di-O-methyl-beta-D-glucopyranosyl epitope for the serodiagnosis of leprosy.
TLDR
3,6-di-O-methyl-beta-D-glucopyranose in its cyclic hemiacetal form is necessary for binding anti-glycolipid IgM from leprosy patients and the prospects of a fully synthetic specific antigen for the worldwide serodiagnosis of lepropsy look promising.
Chemical synthesis and seroreactivity of O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl- alpha-L-rhamnopyranosyl)-(1----9)-oxynonanoyl-bovine serum albumin--the leprosy-specific, natural disaccharide-octyl-neoglycoprotein.
Synthesis of mono- and di-benzyl ethers of benzyl α-l-rhamnopyranoside
The introduction of unsaturated linkages into some carbohydrates and alditol derivatives
Use of synthetic glycoconjugates containing the Mycobacterium leprae specific and immunodominant epitope of phenolic glycolipid I in the serology of leprosy.
TLDR
A synthetic conjugate which contains the intact disaccharide region of PG-I may provide the most sensitive antigen for the large scale serodiagnosis of leprosy.
Synthesis of allyl and benzyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-l-rhamnopyranoside
Analysis of the major antigenic determinants of the characteristic phenolic glycolipid from Mycobacterium leprae.
TLDR
Findings suggest that the cross-reactivity is associated with the phenol ring and implies the disaccharide may be a unique antigenic determinant of M. leprae.
13C nmr study of α- and β-anomeric pairs of d-mannopyranosides and l-rhamnopyranosides
Lymphocyte suppression in leprosy induced by unique M. leprae glycolipid
TLDR
It is shown that a unique antigen of M. leprae is capable of inducing suppression of mitogenic responses of lepromatous patients' lymphocytes in vitro and evidence that the suppressor T cells recognize the specific terminal trisaccharide moiety is provided.
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