A New and Useful Method for the Macrocyclization of Linear Peptides

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• 作者：Allyn T. Londregan ; Kathleen A. Farley ; Chris Limberakis ; Patrick B. Mullins ; David W. Piotrowski
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：June 1, 2012
• 年：2012
• 卷：14
• 期：11
• 页码：2890-2893
• 全文大小：248K
• 年卷期：v.14,no.11(June 1, 2012)
• ISSN：1523-7052

文摘

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鈥揙鈥揇 ring system of vancomycin.