Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans

Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans
Ruitong Wang, Lei Lin, Victor L. Schultz, Robert J. Linhardt, So Young Kim, Xiaorui Han, Paul L. DeAngelis, Dixy E. Green, Alexander Yaksic, Xing Zhang
Unnatural chemically modified nucleotide sugars UDP-4-N3-GlcNAc and UDP-4-N3-GalNAc were chemically synthesized for the first time. These unnatural UDP sugar products were then tested for incorporation into hyaluronan, heparosan, or chondroitin using polysaccharide synthases. UDP-4-N3-GlcNAc served as a chain termination substrate for hyaluronan or heparosan synthases; the resulting 4-N3-GlcNAc-terminated hyaluronan and heparosan were then successfully conjugated with Alexa Fluor 488 DIBO alkyne, demonstrating that this approach is generally applicable for labeling and detection of suitable glycosaminoglycans.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01787

DOI: 10.1021/acs.joc.7b01787

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