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  • Title: A new and useful method for the macrocyclization of linear peptides.
    Author: Londregan AT, Farley KA, Limberakis C, Mullins PB, Piotrowski DW.
    Journal: Org Lett; 2012 Jun 01; 14(11):2890-3. PubMed ID: 22612479.
    Abstract:
    A new and useful procedure for the macrocyclization of linear peptides is described. The natural amino acid side chains of tyrosine (phenol), lysine (alkylamine), and histidine (imidazole) react in an intramolecular fashion with a pendent pyridine-N-oxide-carboxamide, which is selectively activated by the phosphonium salt, PyBroP. The reaction is mild, rapid, and efficient with a potentially large substrate scope. Multiple examples are provided with full characterization and analyses, including a novel aza-variant of the C-O-D ring system of vancomycin.
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