Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid–hydroxylamine (KAHA) ligation† †Electronic supplementary information (ESI) available: Experimental procedures, supplementary results, and spectroscopic data for new compounds. See DOI: 10.1039/c7sc00789b Click here for additional data file.

نویسندگان

  • Florian Rohrbacher
  • André Zwicky
  • Jeffrey W. Bode
چکیده

An antibacterial cyclic AS-48 protein was chemically synthesized by a-ketoacid–hydroxylamine (KAHA) ligation. Initial challenges associated with the exceptionally hydrophobic segments arising from the amphiphilic nature of the protein were resolved by the development of bespoke reaction conditions for hydrophobic segments, using hexafluoroisopropanol (HFIP) as a co-solvent. The synthetic protein displays similar biological activity and properties to those of the native protein. To support the current understanding of its antibacterial mode of action, we demonstrate the ability of AS-48 to be incorporated into synthetic multilamellar vesicles (MLVs).

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منابع مشابه

Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid-hydroxylamine (KAHA) ligation.

An antibacterial cyclic AS-48 protein was chemically synthesized by α-ketoacid-hydroxylamine (KAHA) ligation. Initial challenges associated with the exceptionally hydrophobic segments arising from the amphiphilic nature of the protein were resolved by the development of bespoke reaction conditions for hydrophobic segments, using hexafluoroisopropanol (HFIP) as a co-solvent. The synthetic protei...

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Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system† †Electronic supplementary information (ESI) available: Experimental procedures and characterization of all new compounds. CCDC 1401582. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01909e Click here for additional data file. Click here for additional data file.

Taddol-based phosphoramidite ligands enable enantioselective palladium(0)-catalyzed C–H arylation of cyclopropanes. The cyclized products are obtained in high yields and enantioselectivities. The reported method provides efficient access to a broad range of synthetically attractive cyclopropyl containing dihydroquinolones and dihydroisoquinolones as well as allows for an efficient enantioselect...

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عنوان ژورنال:

دوره 8  شماره 

صفحات  -

تاریخ انتشار 2017