title: α-Azido Acids in Solid-Phase Peptide Synthesis: Compatibility with Fmoc Chemistry and an Alternative Approach to the Solid Phase Synthesis of Daptomycin Analogs.
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.
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.
authors.forename: Chuda Raj
authors.initials: CR
authors.lastname: Lohani
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.
authors.forename: Benjamin
authors.initials: B
authors.lastname: Rasera
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.
authors.forename: Bradley
authors.initials: B
authors.lastname: Scott
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.
authors.forename: Michael
authors.initials: M
authors.lastname: Palmer
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario Canada , N2L 3G1.
authors.forename: Scott D
authors.initials: SD
authors.lastname: Taylor
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D017576:Daptomycin / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000596:Amino Acids; D007202:Indicators and Reagents; D010455:Peptides; D017576:Daptomycin