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Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans
Author(s) -
Xing Zhang,
Dixy E. Green,
Victor Schultz,
Lei Lin,
Xiaorui Han,
Ruitong Wang,
Alexander Yaksic,
So Young Kim,
Paul L. DeAngelis,
Robert J. Linhardt
Publication year - 2017
Publication title -
the journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.7b01787
Subject(s) - chemistry , glycosaminoglycan , uridine diphosphate , uridine , uridine diphosphate glucose , nucleotide sugar , alexa fluor , nucleotide , alkyne , chondroitin , substrate (aquarium) , stereochemistry , biochemistry , polysaccharide , rna , enzyme , fluorescence , physics , quantum mechanics , gene , catalysis , oceanography , geology
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.

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