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• W2050538096 endingPage "8422" @default.
• W2050538096 startingPage "8415" @default.
• W2050538096 abstract "Semisynthesis of natural product derivatives combines the power of fermentation with orthogonal chemical reactions. Yet, chemical modification of complex structures represents an unmet challenge, as poor selectivity often undermines efficiency. The complex antibiotic teicoplanin eradicates bacterial infections. However, as resistance emerges, the demand for improved analogues grows. We have discovered chemical reactions that achieve site-selective alteration of teicoplanin. Utilizing peptide-based additives that alter reaction selectivities, certain bromo-teicoplanins are accessible. These new compounds are also scaffolds for selective cross-coupling reactions, enabling further molecular diversification. These studies enable two-step access to glycopeptide analogues not available through either biosynthesis or rapid total chemical synthesis alone. The new compounds exhibit a spectrum of activities, revealing that selective chemical alteration of teicoplanin may lead to analogues with attenuated or enhanced antibacterial properties, in particular against vancomycin- and teicoplanin-resistant strains." @default.
• W2050538096 created "2016-06-24" @default.
• W2050538096 creator A5059935626 @default.
• W2050538096 creator A5073335566 @default.
• W2050538096 date "2013-05-21" @default.
• W2050538096 modified "2023-09-27" @default.
• W2050538096 title "Chemical Tailoring of Teicoplanin with Site-Selective Reactions" @default.
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• W2050538096 doi "https://doi.org/10.1021/ja4038998" @default.
• W2050538096 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3800266" @default.
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• W2050538096 hasPublicationYear "2013" @default.
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