ArticleAdvanced synthesis & catalysis2008
Chemoenzymatic Syntheses of Tumor-Associated Carbohydrate Antigen Globo-H and Stage-Specific Embryonic Antigen 4.
Article in Advanced synthesis & catalysis, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Stereoconvergent and Chemoenzymatic Synthesis of Tumor-Associated Glycolipid Disialosyl Globopentaosylceramide for Probing the Binding Affinity of Siglec-7.ACS central science · 2024Article
- Synthesis and immunological evaluation ofRSC medicinal chemistry · 2021Article
- Chemoenzymatic synthesis of the oligosaccharide moiety of the tumor-associated antigen disialosyl globopentaosylceramide.Organic & biomolecular chemistry · 2019Article
- Benzene constructionChemical science · 2019Article
- Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans.The Journal of organic chemistry · 2016Article
- Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms.Chemical communications (Cambridge, England) · 2015Article
- One-pot multienzyme synthesis of Lewis x and sialyl Lewis x antigens.Current protocols in chemical biology · 2012Article
- Highly efficient chemoenzymatic synthesis of β1-3-linked galactosides.Chemical communications (Cambridge, England) · 2010Article
- Recent progress in chemical and chemoenzymatic synthesis of carbohydrates.Current opinion in chemical biology · 2009Review
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Authors and funding
10 authors.
Funding
Abstract
Gangliosides have attracted much attention due to their important biological properties. Herein, we report the first chemoenzymatic syntheses of two globo series of ganglioside oligosaccharides, Globo-H 1 and stage-specific embryonic antigen-4 (SSEA-4) 2. The common precursor SSEA-3 pentasaccharide for these two compounds was assembled rapidly using the pre-activation based one-pot glycosylation method. The stereoselectivity in forming the 1,2-cis linkage in SSEA-3 was attributed to a steric buttressing effect of the donor rather than electronic properties of the glycosyl donors. SSEA-3 was then successfully fucosylated by the fucosyltransferase WbsJ and sialylated by sialyltransferases CST-I and PmST1 producing Globo-H and SSEA-4 respectively.
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Registered trials
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