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β-D-Mannosyl phosphomycoketide

Mycoketide Edmund
Edmund Yeh


β-D-Mannosyl phosphomycoketide (MPM) 1 and 2 were first isolated from the cell walls of Mycobacterium tuberculosis and Mycobacterium avium by Moody and coworkers in 2000.1 Both MPM-1 and MPM-2 were shown to interact strongly with Cluster Differentiation 1c (CD1c) antigen presenting protein, which played a pivotal role in T-cell activation in the event of a tuberculosis infection. There have only been two previous total syntheses completed on this molecule, however the absolute orientations of the methyl branches in this natural product are still unknown.2,3 We plan to utilize fluorous mixture synthesis (FMS) to complete the synthesis of all 32 isomers and identify the absolute stereochemistry of the natural product.

References

1. Moody, D.B.; Ulrichs, T.; Muhlecker, W.; Young, D. C.; Gurcha, S. S.; Grant, E.; Rosat, J.-P.; Brenner, M. B.; Costello, C. E.; Besra, G. S.; Porcelli, S. A. Nature 2000, 404, 884-888.

2. Crich, D.; Dudkin, V. J. Am. Chem. Soc. 2002, 124, 2263-2266.

3. Van Summeren, R. P.; Moody, D. B.; Feringa, B. L.; Minnaard, A. J. J. Am. Chem. Soc. 2006, 128, 4546-4547.