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U.S. Department of Health and Human Services

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ACS Synth Biol 2019 Nov 15;8(11):2507-13

Synthesis and characterization of versatile O-glycan precursors for cellular O-glycomics.

Zhang Q, Li Z, Chernova T, Saikam V, Cummings R, Song X, Ju T, Smith DF, Wang PG


Protein O-glycosylation is a universal post-translational modification and plays essential roles in many biological processes. Recently we reported a technology termed cellular O-glycome reporter/amplification (CORA) to amplify and profile mucin-type O-glycans of living cells growing in the presence of peracetylated Benzyl-alpha-GalNAc (Ac3GalNAc-alpha-Bn). However, the application and development of the CORA method are limited by the properties of the precursor benzyl aglycone, which is relatively inert to further chemical modifications. Here we described a rapid parallel microwave-assisted synthesis of Ac3GalNAc-alpha-Bn derivatives to identify versatile precursors for cellular O-glycomics. In total, 26 derivatives, including fluorescent and bioorthogonal reactive ones, were successfully synthesized. The precursors were evaluated for their activity as acceptors for T-synthase and for their ability to function as CORA precursors. Several of the precursors possessing useful functional groups were more efficient than Ac3GalNAc-alpha-Bn as T-synthase acceptors and cellular O-glycome reporters. These precursors will advance the CORA technology for studies of functional O-glycomics.

Category: Journal Article
PubMed ID: #31638776 DOI: 10.1021/acssynbio.9b00168
Includes FDA Authors from Scientific Area(s): Drugs
Entry Created: 2019-12-29