Synthesis of 4-azido-N-acetylhexosamine uridine diphosphate donors: Clickable glycosaminoglycans

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Authors
Zhang, Xing
Green, Dixy E.
Schultz, Victor L.
Lin, Lei
Han, Xiaorui
Wang, Ruitong
Yaksic, Alexander
Kim, So Young
Deangelis, Paul L.
Linhardt, Robert J.
Issue Date
2017-09-15
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Research Projects
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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.
Description
Journal of Organic Chemistry 82, 9910−9915
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Full Citation
Synthesis of 4-azido-N-acetylhexosamine uridine diphosphate donors: Clickable glycosaminoglycans, X. Zhang, D.E. Green, V.L. Schultz, L. Lin, X.Han, R. Wang, A. Yaksic, S.Y. Kim, P. L. DeAngelis, R. J. Linhardt, Journal of Organic Chemistry 82, 9910−9915, 2017.
Publisher
American Chemical Society (ACS)
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Volume
Issue
PubMed ID
DOI
ISSN
15206904
223263
EISSN