Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 16, Pages 6743-6759Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301189y
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Funding
- IRL Charitable Trust
- University of Otago
- New Zealand Ministry of Science and Innovation [C08X0808]
- New Zealand Ministry of Business, Innovation & Employment (MBIE) [C08X0808] Funding Source: New Zealand Ministry of Business, Innovation & Employment (MBIE)
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A family of naturally occurring mycobacterial phosphatidylinositol (PI) and its dimannosides (PIM2, AcPIM2., and Ac2PIM2) 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.
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