Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis.
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.
Liu
Xinyu
X
Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich Wolfgang-Pauli-Str. 10, HCI F315, 8093 Zürich, Switzerland.
Stocker
Bridget L
BL
Seeberger
Peter H
PH
D002240:Carbohydrate Sequence; D006031:Glycosylation; D008358:Mannose / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009169:Mycobacterium tuberculosis / Q000737:chemistry / Q000378:metabolism*; D010716:Phosphatidylinositols / Q000138:chemical synthesis*
D008362:Mannosides; D010716:Phosphatidylinositols; C034154:phosphatidylinositol mannoside; D008358:Mannose