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

• Type of Material: Article
• Authors: Yuyang Zhu, Emory University; Xeuyun Liu, Emory University; Ying Zhang, Emory University; Zhongfu Wang, Northwest University; Yi Lasanajak, Emory University; Xuezheng Song, Emory University
• Language: English
• Date: 2018-11-01
• Publisher: American Chemical Society
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © 2018 American Chemical Society.
• Final Published Version (URL): http://dx.doi.org/10.1021/acs.bioconjchem.8b00678
• Title of Journal or Parent Work: Bioconjugate Chemistry
• ISSN: 1043-1802
• Volume: 29
• Issue: 11
• Start Page: 3847
• End Page: 3855
• Grant/Funding Information: This work was supported by NIH Common Fund Glyco-science (U01GM116254) and partially by a STTR grant R41GM122139.
• Keywords: DERIVATIZATION; Chemistry; Chemistry, Multidisciplinary; HIGH-MANNOSE; NATURAL GLYCANS; Chemistry, Organic; OXIDATIVE RELEASE; Biochemistry & Molecular Biology; AMIDE BOND FORMATION; MICROARRAY STRATEGY; PEPTIDE; Biochemical Research Methods; GLYCOSYLATION; Physical Sciences; Science & Technology; SIALIC ACIDS; Life Sciences & Biomedicine; OLIGOSACCHARIDE
• Research Categories: Chemistry, Organic; Chemistry, Biochemistry; Biology, Molecular

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.