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J Org Chem. 2017 Sep 15;82(18):9910-9915. doi: 10.1021/acs.joc.7b01787. Epub 2017 Aug 25.

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

Author information

1
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
2
Department of Biochemistry and Molecular Biology, University of Oklahoma Health Sciences Center , 940 Stanton L. Young Boulevard, Oklahoma City, Oklahoma 73126, United States.

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.

PMID:
28813597
DOI:
10.1021/acs.joc.7b01787
[Indexed for MEDLINE]

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