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Synthetic Polyprenol-Pyrophosphate Linked Oligosaccharides Are Efficient Substrates for Mycobacterial Galactan Biosynthetic Enzymes
Download2019-01-31
Xiaochao Xue, Ruixiang Blake Zheng, Akihiko Koizumi, Ling Han, John S. Klassen, Todd L. Lowary
Mycobacteria, including the human pathogen Mycobacterium tuberculosis, produce a complex cell wall that is critical for their survival. The largest structural component of the cell wall, the mycolylarabinogalactanpeptidoglycan complex, has at its core a galactan domain composed of D
-galactofuranose residues. Mycobacterial galactan biosynthesis has been proposed to involve two glycosyltransferases, GlfT1 and GlfT2, which elongate polyprenol-pyrophosphate linked glycosyl acceptor substrates using UDP-galactofuranose as the donor substrate. We here report the first chemical synthesis of GlfT1
and demonstrate a straightforward route for the preparation of such compounds. The work also provides additional support for the process by which this important glycan is biosynthesized using, for the first time, close structural analogs to the natural substrates.