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Unnatural chemically modified nucleotide sugars UDP-4-N 3 -GlcNAc and UDP-4-N 3 -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-N 3 -GlcNAc served as a chain termination substrate for hyaluronan or heparosan synthases; the resulting 4-N 3 -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.

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