ArticleCarbohydrate research2008
Introducing N-glycans into natural products through a chemoenzymatic approach.
Article in Carbohydrate research, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 41 citations in OpenAlex.
- Synthesis of Four Pentacyclic Triterpene-Sialylglycopeptide Conjugates and Their Affinity Assays with Hemagglutinin.Molecules (Basel, Switzerland) · 2021Article
- Separation and preparation of N-glycans based on ammonia-catalyzed release method.Glycoconjugate journal · 2020Article
- Chemoenzymatic Methods for the Synthesis of Glycoproteins.Chemical reviews · 2018Review
- Synthesis of Glycosides by Glycosynthases.Molecules (Basel, Switzerland) · 2017Review
- Optimal Synthetic Glycosylation of a Therapeutic Antibody.Angewandte Chemie (International ed. in English) · 2016Article
- Optimal Synthetic Glycosylation of a Therapeutic Antibody.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2016Article
- Convergent chemo-enzymatic synthesis of mannosylated glycopeptides; targeting of putative vaccine candidates to antigen presenting cells.Chemical science · 2015Article
- Synthetic glycopeptides reveal the glycan specificity of HIV-neutralizing antibodies.Nature chemical biology · 2013Article
- A two-step enzymatic glycosylation of polypeptides with complex N-glycans.Bioorganic & medicinal chemistry · 2013Article
- The Amazing Transglycosylation Activity of Endo-β-N-acetylglucosaminidases.Trends in glycoscience and glycotechnology : TIGG · 2011Article
- Chemoenzymatic synthesis and lectin array characterization of a class of N-glycan clusters.Journal of the American Chemical Society · 2009Article
- Enzymatic transglycosylation for glycoconjugate synthesis.Current opinion in chemical biology · 2009Review
- Context-specific target definition in influenza a virus hemagglutinin-glycan receptor interactions.Chemistry & biology · 2009Article
- Enzymatic glycosylation of triazole-linked GlcNAc/Glc-peptides: synthesis, stability and anti-HIV activity of triazole-linked HIV-1 gp41 glycopeptide C34 analogues.Chembiochem : a European journal of chemical biology · 2009Article
- Endo-beta-N-acetylglucosaminidase-catalyzed polymerization of beta-Glcp-(1-->4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation.Carbohydrate research · 2009Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The present study describes an efficient chemoenzymatic method for introducing a core N-glycan of glycoprotein origin into various lipophilic natural products. It was found that the endo-beta-N-acetylglucosaminidase from Arthrobactor protophormiae (Endo-A) had broad substrate specificity and can accommodate a wide range of glucose (Glc)- or N-acetylglucosamine (GlcNAc)-containing natural products as acceptors for transglycosylation, when an N-glycan oxazoline was used as a donor substrate. Using lithocholic acid as a model compound, we have shown that introduction of an N-glycan could be achieved by a two-step approach: chemical glycosylation to introduce a monosaccharide (Glc or GlcNAc) as a handle, and then Endo-A catalyzed transglycosylation to accomplish the site-specific N-glycan attachment. For those natural products that already carry terminal Glc or GlcNAc residues, direct enzymatic transglycosylation using sugar oxazoline as the donor substrate was achievable to introduce an N-glycan. It was also demonstrated that simultaneous double glycosylation could be fulfilled when the natural product contains two Glc residues. This chemoenzymatic method is concise, site-specific, and highly convergent. Because N-glycans of glycoprotein origin can serve as ligands for diverse lectins and cell-surface receptors, introduction of a defined N-glycan into biologically significant natural products may bestow novel properties onto these natural products for drug discovery and development.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.