Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate

K N Jayaprakash; Jun Lu; Bert Fraser-Reid

doi:10.1016/j.bmcl.2004.04.103

Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate

Bioorg Med Chem Lett. 2004 Jul 16;14(14):3815-9. doi: 10.1016/j.bmcl.2004.04.103.

Authors

K N Jayaprakash¹, Jun Lu, Bert Fraser-Reid

Affiliation

¹ Natural Products and Glycotechnology Research Institute, Inc., (NPG), 4118 Swarthmore Road, Durham, NC 27706, USA.

PMID: 15203168
DOI: 10.1016/j.bmcl.2004.04.103

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Glycosylation
Inositol / chemistry
Lipids / chemistry
Mycobacterium tuberculosis / classification
Mycobacterium tuberculosis / metabolism*
Phosphatidylinositols / chemical synthesis*
Phosphatidylinositols / pharmacology
Trisaccharides / chemistry

Substances

Lipids
Phosphatidylinositols
Trisaccharides
Inositol