Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate.
Regioselective mannosylations of a myoinositol acceptor diol are readily achieved by Lewis acid mediated iodinolysis of n-pentenyl ortho-esters. The procedure affords a psuedotrisaccharide to which the phosphoglyceryl and other lipid residues are added leading to the key biosynthetic intermediate of Mycobacterium species.
Jayaprakash
K N
KN
Natural Products and Glycotechnology Research Institute, Inc., (NPG), 4118 Swarthmore Road, Durham, NC 27706, USA.
Lu
Jun
J
Fraser-Reid
Bert
B
D006031:Glycosylation; D007294:Inositol / Q000737:chemistry; D008055:Lipids / Q000737:chemistry; D009169:Mycobacterium tuberculosis / Q000145:classification / Q000378:metabolism*; D010716:Phosphatidylinositols / Q000138:chemical synthesis* / Q000494:pharmacology; D014312:Trisaccharides / Q000737:chemistry
D008055:Lipids; D010716:Phosphatidylinositols; D014312:Trisaccharides; D007294:Inositol