ArticleChembiochem : a European journal of chemical biology2009
Enzymatic glycosylation of triazole-linked GlcNAc/Glc-peptides: synthesis, stability and anti-HIV activity of triazole-linked HIV-1 gp41 glycopeptide C34 analogues.
Article in Chembiochem : a European journal of chemical biology, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 40 citations in OpenAlex.
- A Literature Review Focusing on the Antiviral Activity of [1,2,4] and [1,2,3]-triazoles.Mini reviews in medicinal chemistry · 2024Review
- Glycosylation and Lipidation Strategies: Approaches for Improving Antimicrobial Peptide Efficacy.Pharmaceuticals (Basel, Switzerland) · 2023Review
- Synthetic Glycobiology: Parts, Systems, and Applications.ACS synthetic biology · 2020Review
- Mannosylated hemagglutinin peptides bind cyanovirin-N independent of disulfide-bonds in complementary binding sites.RSC advances · 2020Article
- Enfuvirtide-PEG conjugate: A potent HIV fusion inhibitor with improved pharmacokinetic properties.European journal of medicinal chemistry · 2016Article
- Glycosylation, an effective synthetic strategy to improve the bioavailability of therapeutic peptides.Chemical science · 2016Article
- Chemoenzymatic Fc glycosylation via engineered aldehyde tags.Bioconjugate chemistry · 2014Article
- Directed evolution of multivalent glycopeptides tightly recognized by HIV antibody 2G12.Journal of the American Chemical Society · 2014Article
- Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions.Chemistry & biology · 2014Review
- Synthetic glycopeptides and glycoproteins with applications in biological research.Beilstein journal of organic chemistry · 2012Article
- Convergent synthesis of homogeneous Glc1Man9GlcNAc2-protein and derivatives as ligands of molecular chaperones in protein quality control.Journal of the American Chemical Society · 2011Article
- Secreted antiviral entry inhibitory (SAVE) peptides for gene therapy of HIV infection.Molecular therapy : the journal of the American Society of Gene Therapy · 2011Article
- 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
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 3 countries.
Funding
Abstract
Long-lasting sweet proteins: The chemoenzymatic synthesis of a triazole (T)-linked glycosylated C34 fragment from HIV-1 gp41 is described. The glycopeptide shows high solubility, excellent fusion inhibition, and as shown in the graph, promising protease resistance. Endoglycosidase-catalyzed transglycosylation of triazole-linked glucose (Glc) and N-acetylglucosamine (GlcNAc)-containing dipeptides and polypeptides was achieved by using synthetic sugar oxazoline as the donor substrate. It was found that both N- and C-linked Glc/GlcNAc-containing triazole derivatives were effective substrates for endo-beta-N-acetylglucosaminidase from Arthrobacter (Endo-A) for transglycosylation; this demonstrates a broad acceptor substrate specificity for Endo-A. This chemoenzymatic method was successfully used for the synthesis of a novel triazole-linked C34 glycopeptide derived from the HIV-1 envelope glycoprotein, gp41. We found that the synthetic C34 glycopeptide possesses potent anti-HIV activity with an IC(50) of 21 nM. The triazole-linked C34 glycopeptide demonstrated a much enhanced stability against protease- and glycoamidase-catalyzed digestion; this shows the protective effects of glycosylation and the stability of the triazole linkage. These favorable properties suggest that the triazole-linked C34 glycopeptide might be valuable for further development as an anti-HIV drug candidate.
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