Chemoenzymatic synthesis of UDP-GlcNAc and UDP-GalNAc analogs for the preparation of unnatural glycosaminoglycans

Masuko, S.
Bera, S.
Green, D.E.
Weïwer, M.
DeAngelis, P.L.
Linhardt, Robert J.
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Chemoenzymatic synthesis of UDP-GlcNAc and UDP-GalNAc analogs for the preparation of unnatural glycosaminoglycans, S. Masuko, S. Bera, D. E. Green, M. Weïwer, P. L. DeAngelis, R. J. Linhardt, Journal of Organic Chemistry, 77, 1449-1456, 2012.
Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to non-immobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.
Journal of Organic Chemistry, 77, 1449-1456
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