ArticleThe Journal of organic chemistry2014
X-ray crystal structure of teicoplanin A₂-2 bound to a catalytic peptide sequence via the carrier protein strategy.
Article in The Journal of organic chemistry, 2014. 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, 22 citations in OpenAlex.
- Novel insights into the dependence of adsorption-desorption kinetics on particle geometry in chiral chromatography.Analytical and bioanalytical chemistry · 2024Article
- Environmentally Sustainable Achiral and Chiral Chromatographic Analysis of Amino Acids in Food Supplements.Molecules (Basel, Switzerland) · 2022Article
- Bacteriophage Lytic Enzyme P9ly as an Alternative Antibacterial Agent Against Antibiotic-ResistantFrontiers in microbiology · 2022Article
- Late-Stage Diversification of Natural Products.ACS central science · 2020Review
- Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.Chemical reviews · 2017Review
- Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis.Accounts of chemical research · 2017Article
- A stepwise dechlorination/cross-coupling strategy to diversify the vancomycin 'in-chloride'.Bioorganic & medicinal chemistry letters · 2016Article
- Structure diversification of vancomycin through peptide-catalyzed, site-selective lipidation: a catalysis-based approach to combat glycopeptide-resistant pathogens.Journal of medicinal chemistry · 2015Article
- Transition states. Trapping a transition state in a computationally designed protein bottle.Science (New York, N.Y.) · 2015Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
We report the X-ray crystal structure of a site-selective peptide catalyst moiety and teicoplanin A2-2 complex. The expressed protein ligation technique was used to couple T4 lysozyme (T4L) and a synthetic peptide catalyst responsible for the selective phosphorylation of the N-acetylglucosamine sugar in a teicoplanin A2-2 derivative. The T4L-Pmh-dPro-Aib-dAla-dAla construct was crystallized in the presence of teicoplanin A2-2. The resulting 2.3 Å resolution protein-peptide-teicoplanin complex crystal structure revealed that the nucleophilic nitrogen of N-methylimidazole in the Pmh residue is in closer proximity (7.6 Å) to the N-acetylglucosamine than the two other sugar rings present in teicoplanin (9.3 and 20.3 Å, respectively). This molecular arrangement is consistent with the observed selectivity afforded by the peptide-based catalyst when it is applied to a site-selective phosphorylation reaction involving a teicoplanin A2-2 derivative.
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