ArticleJournal of the American Chemical Society2009
Chemoenzymatic synthesis of GD3 oligosaccharides and other disialyl glycans containing natural and non-natural sialic acids.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 46 papers.
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Who cites it
46 citing papers in PubMed, 120 citations in OpenAlex.
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- GlycoRNA research: from unknown unknowns to known unknowns.Protein & cell · 2026Review
- Chemoenzymatically Synthesized O-Acetylated GD3 Gangliosides to Examine Viral Receptor Specificities in a Cellular Context.Angewandte Chemie (International ed. in English) · 2026Article
- Human coronavirus HKU1 spike structures reveal the basis for sialoglycan specificity and carbohydrate-promoted conformational changes.Nature communications · 2025Article
- A New Strategy to Functionalize Exosomes via Enzymatic Engineering of Surface Glycans and its Application to Profile Exosomal Glycans and Endocytosis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Efficient Enzymatic Glycan Engineering of Extracellular Vesicles Using Nanomaterial-Interfaced Microfluidics.ACS applied materials & interfaces · 2025Article
- Comprehensive Modular Synthesis of Ganglioside Glycans and Evaluation of their Binding Affinities to Siglec-7 and Siglec-9.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Integrated chemoenzymatic synthesis of a comprehensive sulfated ganglioside glycan library to decipher functional sulfoglycomics and sialoglycomics.Nature chemistry · 2024Article
- Influenza D virus utilizes both 9-Journal of virology · 2024Article
- Enabling Chemoenzymatic Strategies and Enzymes for Synthesizing Sialyl Glycans and Sialyl Glycoconjugates.Accounts of chemical research · 2024Article
- Genetically encoded chemical crosslinking of carbohydrate.Nature chemistry · 2023Article
- Enzymatic glycoengineering-based spin labelling of cell surface sialoglycans to enable their analysis by electron paramagnetic resonance (EPR) spectroscopy.The Analyst · 2022Article
- One-pot multienzyme (OPME) chemoenzymatic synthesis of brain ganglioside glycans with human ST3GAL II expressed inChemCatChem · 2022Article
- Engineering analysis of multienzyme cascade reactions for 3'-sialyllactose synthesis.Biotechnology and bioengineering · 2021Article
- Synthetic O-acetylated sialosides facilitate functional receptor identification for human respiratory viruses.Nature chemistry · 2021Article
- A Chemoenzymatic Synthon Strategy for SynthesizingThe Journal of organic chemistry · 2020Article
- Chemoenzymatic Synthesis ofJournal of the American Chemical Society · 2020Article
- A combined NMR, MD and DFT conformational analysis of 9-O-acetyl sialic acid-containing GM3 ganglioside glycan and its 9-N-acetyl mimic.Glycobiology · 2020Article
- Catalytic Cycle ofBiochemistry · 2020Article
- Recent Progress in Chemo-Enzymatic Methods for the Synthesis of N-Glycans.Frontiers in chemistry · 2020Review
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Authors and funding
9 authors at 1 institution in 1 country.
Funding
Abstract
In order to understand the biological importance of naturally occurring sialic acid variations on disialyl structures in nature, we developed an efficient two-step multienzyme approach for the synthesis of a series of GD3 ganglioside oligosaccharides and other disialyl glycans containing a terminal Siaalpha2-8Sia component with different natural and non-natural sialic acids. In the first step, alpha2-3- or alpha2-6-linked monosialylated oligosaccharides were obtained using a one-pot three-enzyme approach. These compounds were then used as acceptors for the alpha2-8-sialyltransferase activity of a recombinant truncated multifunctional Campylobacter jejuni sialyltransferase CstII mutant, CstIIDelta32(I53S), to produce disialyl oligosaccharides. The alpha2-8-sialyltransferase activity of CstIIDelta32(I53S) has promiscuous donor substrate specificity and can tolerate various substitutions at C-5 or C-9 of the sialic acid in CMP-sialic acid, while its acceptor substrate specificity is relatively restricted. The terminal sialic acid residues in the acceptable monosialylated oligosaccharide acceptors are restricted to Neu5Ac, Neu5Gc, KDN, and some of their C-9-modified forms but not their C-5 derivatives. The disialyl oligosaccharides obtained are valuable probes for their biological studies.
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