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

Xing Zhang, Dixy E. Green, Victor L. Schultz, Lei Lin, Xiaorui Han, Ruitong Wang, Alexander Yaksic, So Young Kim, Paul L. Deangelis, Robert J. Linhardt

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)9910-9915
Number of pages6
JournalJournal of Organic Chemistry
Volume82
Issue number18
DOIs
StatePublished - 15 Sep 2017
Externally publishedYes

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