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J Org Chem. 2016 Mar 18;81(6):2624-8. doi: 10.1021/acs.joc.5b02882. Epub 2016 Mar 3.

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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1
Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.

Abstract

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.

PMID:
26938305
DOI:
10.1021/acs.joc.5b02882
[Indexed for MEDLINE]
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