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

Publication ,  Journal Article
Zhang, X; Green, DE; Schultz, VL; Lin, L; Han, X; Wang, R; Yaksic, A; Kim, SY; DeAngelis, PL; Linhardt, RJ
Published in: J Org Chem
September 15, 2017

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.

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Published In

J Org Chem

DOI

EISSN

1520-6904

Publication Date

September 15, 2017

Volume

82

Issue

18

Start / End Page

9910 / 9915

Location

United States

Related Subject Headings

  • Uridine Diphosphate
  • Organic Chemistry
  • Molecular Conformation
  • Hexosamines
  • Glycosaminoglycans
  • Click Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

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Zhang, X., Green, D. E., Schultz, V. L., Lin, L., Han, X., Wang, R., … Linhardt, R. J. (2017). Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans. J Org Chem, 82(18), 9910–9915. https://doi.org/10.1021/acs.joc.7b01787
Zhang, Xing, Dixy E. Green, Victor L. Schultz, Lei Lin, Xiaorui Han, Ruitong Wang, Alexander Yaksic, So Young Kim, Paul L. DeAngelis, and Robert J. Linhardt. “Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans.J Org Chem 82, no. 18 (September 15, 2017): 9910–15. https://doi.org/10.1021/acs.joc.7b01787.
Zhang X, Green DE, Schultz VL, Lin L, Han X, Wang R, et al. Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans. J Org Chem. 2017 Sep 15;82(18):9910–5.
Zhang, Xing, et al. “Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans.J Org Chem, vol. 82, no. 18, Sept. 2017, pp. 9910–15. Pubmed, doi:10.1021/acs.joc.7b01787.
Zhang X, Green DE, Schultz VL, Lin L, Han X, Wang R, Yaksic A, Kim SY, DeAngelis PL, Linhardt RJ. Synthesis of 4-Azido-N-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans. J Org Chem. 2017 Sep 15;82(18):9910–9915.
Journal cover image

Published In

J Org Chem

DOI

EISSN

1520-6904

Publication Date

September 15, 2017

Volume

82

Issue

18

Start / End Page

9910 / 9915

Location

United States

Related Subject Headings

  • Uridine Diphosphate
  • Organic Chemistry
  • Molecular Conformation
  • Hexosamines
  • Glycosaminoglycans
  • Click Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry