869213-46-7Relevant academic research and scientific papers
Synthesis and mass spectral characterization of mycobacterial phosphatidylinositol and its dimannosides
Rankin, Gregory M.,Compton, Benjamin J.,Johnston, Karen A.,Hayman, Colin M.,Painter, Gavin F.,Larsen, David S.
experimental part, p. 6743 - 6759 (2012/09/25)
A family of naturally occurring mycobacterial phosphatidylinositol (PI) and its dimannosides (PIM2, AcPIM2, and Ac 2PIM2) that all possess the predominant natural 19:0/16:0 phosphatidyl acylation pattern were prepared to study their mass spectral fragmentations. Among these, the first synthesis of a fully lipidated PIM (i.e., (16:0,18:0)(19:0/16:0)-PIM2) was achieved from (±)-1,2:4,5- diisopropylidene-d-myo-inositol in 16 steps in 3% overall yield. A key feature of the strategy was extending the utility of the p-(3,4-dimethoxyphenyl)benzyl protecting group for its use at the O-3 position of inositol to allow installation of the stearoyl residue at a late stage in the synthesis. Mass spectral studies were performed on the synthetic PIMs and compared to those reported for natural PIMs identified from a lipid extract of M. bovis BCG. These analyses confirm that fragmentation patterns can be used to identify the structures of specific PIMs from the cell wall lipid extract.
