Comparison of the solid-phase fragment condensation and phase-change approaches in the synthesis of salmon I calcitonin.
Salmon I calcitonin was synthesized using both phase-change and conventional solid-phase fragment condensation (SPFC) approaches, utilizing the Rink amide linker (Fmoc-amido-2,4-dimethoxybenzyl-4-phenoxyacetic acid) combined with 2-chlorotrityl resin and the Fmoc/tBu(Trt)-based protection scheme. Phase-change synthesis, performed by the selective detachment of the fully protected C-terminal 22-mer peptide-linker from the resin and subsequent condensation in solution with the N-terminal 1-10 fragment, gave a product of slightly less purity (85 vs. 92%) than the corresponding synthesis on the solid-phase. In both cases salmon I calcitonin was easily obtained in high purity.
Gatos
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D
Department of Chemistry, University of Patras, Greece. d.gatos@upatras.gr
Tzavara
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C
D002116:Calcitonin / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D021241:Spectrometry, Mass, Electrospray Ionization
C028815:salmon calcitonin; D002116:Calcitonin