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Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis.
Journal article

Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis.

  • Liu X Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich Wolfgang-Pauli-Str. 10, HCI F315, 8093 Zürich, Switzerland.
  • Stocker BL
  • Seeberger PH
  • 2006-03-16
Published in:
  • Journal of the American Chemical Society. - 2006
Carbohydrate Sequence
Glycosylation
Mannose
Mannosides
Molecular Sequence Data
Mycobacterium tuberculosis
Phosphatidylinositols
English The total synthesis of phosphatidylinositol mannosides (PIMs), a key class of antigenic glycolipids found on the cell wall of Mycobacterium tuberculosis, is described. The synthetic strategy relied on a [4 + 3] glycosylation of tetramannoside 1 and pseudotrisaccharide 2, which allowed for convergent access to the glycan backbone of the phosphatidylinositol dimannoside (PIM2) and hexamannoside (PIM6). A short practical synthesis of tuberculostearic acid was achieved based on a copper-catalyzed cross-coupling reaction. Union of the glycan and lipid parts resulted in the first total synthesis of native PIM2 and PIM6.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/67209
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