Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans

Hai Yu, Yanhong Li, Jie Zeng, Vireak Thon, Dung M. Nguyen, Thao Ly, Hui Yu Kuang, Alice Ngo, Xi Chen

Research output: Contribution to journalArticle

22 Scopus citations

Abstract

Glycosphingolipids are a diverse family of biologically important glycolipids. In addition to variations on the lipid component, more than 300 glycosphingolipid glycans have been characterized. These glycans are directly involved in various molecular recognition events. Several naturally occurring sialic acid forms have been found in sialic acid-containing glycosphingolipids, namely gangliosides. However, ganglioside glycans containing less common sialic acid forms are currently not available. Herein, highly effective one-pot multienzyme (OPME) systems are used in sequential for high-yield and cost-effective production of glycosphingolipid glycans, including those containing different sialic acid forms such as N-acetylneuraminic acid (Neu5Ac), N-glycolylneuraminic acid (Neu5Gc), 2-keto-3-deoxy-d-glycero-d-galacto-nononic acid (Kdn), and 8-O-methyl-N-acetylneuraminic acid (Neu5Ac8OMe). A library of 64 structurally distinct glycosphingolipid glycans belonging to ganglio-series, lacto-/neolacto-series, and globo-/isoglobo-series glycosphingolipid glycans is constructed. These glycans are essential standards and invaluable probes for bioassays and biomedical studies.

Original languageEnglish (US)
Pages (from-to)10809-10824
Number of pages16
JournalJournal of Organic Chemistry
Volume81
Issue number22
DOIs
StatePublished - Nov 18 2016

ASJC Scopus subject areas

  • Organic Chemistry

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    Yu, H., Li, Y., Zeng, J., Thon, V., Nguyen, D. M., Ly, T., Kuang, H. Y., Ngo, A., & Chen, X. (2016). Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans. Journal of Organic Chemistry, 81(22), 10809-10824. https://doi.org/10.1021/acs.joc.6b01905