α-Azido Acids in Solid-Phase Peptide Synthesis: Compatibility with Fmoc Chemistry and an Alternative Approach to the Solid Phase Synthesis of Daptomycin Analogs

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• 作者：Chuda Raj Lohani ; Benjamin Rasera ; Bradley Scott ; Michael Palmer ; Scott D. Taylor
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：81
• 期：6
• 页码：2624-2628
• 全文大小：460K
• ISSN：1520-6904

文摘

α-Azido acids have been used in solid phase peptide synthesis (SPPS) for almost 20 years. Here we report that peptides bearing an N-terminal α-azidoaspartate residue undergo elimination of an azide ion when treated with reagents that are commonly used for removing the Fmoc group during SPPS. We also report an alternative solid-phase route to the synthesis of an analog of daptomycin that uses a reduced number of α-azido amino acids and without elimination of an azide ion.