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. 2016 Nov 18;81(22):10809-10824.
doi: 10.1021/acs.joc.6b01905. Epub 2016 Oct 24.

Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans

Hai Yu  1   2 , Yanhong Li  1   2 , Jie Zeng  2   3 , Vireak Thon  2 , Dung M Nguyen  2 , Thao Ly  2 , Hui Yu Kuang  2 , Alice Ngo  2 , Xi Chen  2
Affiliations

Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans

Hai Yu et al. J Org Chem. .

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.

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Figures

Scheme 1
Scheme 1
Sequential One-Pot Multienzyme (OPME) Synthesis of Ganglio-, Lacto-/Neolacto-, and Globo-/Isoglobo-Series Glycosphingolipid Glycans.
Scheme 2
Scheme 2
Production of GM3 and GD3 Glycans Using OPME α2–3- and α2–8-Sialylation Systems.
Scheme 3
Scheme 3
Synthesis of GM2/GD2 and GM1/GD1b Glycans Containing Neu5Ac, Neu5Gc, Kdn, or Neu5Ac8OMe via One-Pot Multienzyme (OPME) GalNAc and Gal Transfer Systems, Respectively.
Scheme 4
Scheme 4
Synthesis of Lc3, LNnT, and Sialylated LNnT using OPME Glycosylation Systems.
Scheme 5
Scheme 5
Synthesis of Sialylated LNT Using OPME Sialylation Systems.
Scheme 6
Scheme 6
Synthesis of Lex Pentasaccharide and Its Sialylated Forms using OPME Glycosylation Systems.
Scheme 7
Scheme 7
OPME Synthesis of Globo and Isoglobo-Series Glycans.
See this image and copyright information in PMC

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