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Author Notes:

Corresponding Author xsong2@emory.edu. Phone: +1-404-727-3664. Fax: +1-404-727-2738.

We thank Dr. David F. Smith for discussions and comments on the manuscript.

We also acknowledge Emory Comprehensive Glycomics Core (ECGC), which is subsidized by the Emory University School of Medicine and is one of the Emory Integrated Core Facilities.

The authors declare the following competing financial interest(s): X.S. is a cofounder of NatGlycan LLC, which is commercializing the ORNG technology.

Subjects:

Research Funding:

This work was supported by NIH Common Fund Glyco-science (U01GM116254) and partially by a STTR grant R41GM122139.

Keywords:

  • Science & Technology
  • Life Sciences & Biomedicine
  • Physical Sciences
  • Biochemical Research Methods
  • Biochemistry & Molecular Biology
  • Chemistry, Multidisciplinary
  • Chemistry, Organic
  • Chemistry
  • AMIDE BOND FORMATION
  • SIALIC ACIDS
  • MICROARRAY STRATEGY
  • OXIDATIVE RELEASE
  • NATURAL GLYCANS
  • HIGH-MANNOSE
  • DERIVATIZATION
  • GLYCOSYLATION
  • PEPTIDE
  • OLIGOSACCHARIDE

Anthranilic Acid as a Versatile Fluorescent Tag and Linker for Functional Glycomics

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Journal Title:

Bioconjugate Chemistry

Volume:

Volume 29, Number 11

Publisher:

, Pages 3847-3855

Type of Work:

Article | Post-print: After Peer Review

Abstract:

The advancement of glycoscience is critically dependent on the access to a large number of glycans for their functional study. Naturally occurring glycans are considered a viable source for diverse and biologically relevant glycan libraries. A mixture of free reducing glycans released from natural sources can be fluorescently tagged and separated by chromatography to produce a natural glycan library. Anthranilic acid (AA) has been widely used to fluorescently tag reducing glycans for HPLC or LC/MS analysis. However, AA conjugated glycans are not efficiently immobilized on microarray slides due to the lack of a primary alkylamine functional group. In this study, we have developed simple and efficient chemistry for bioconjugation and further functionalization of glycan-AA conjugates. This new approach enables quick preparation of glycan microarrays and neoglycoproteins from glycan-AA conjugates, which can be separated by weak anion exchange (WAX) and C18 reversed-phase HPLC.

Copyright information:

© 2018 American Chemical Society.

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