Synthesis of the15N-Gln11 labeled peptaibol antibiotic zervamicin-IIB
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Synthesis of zervamicin IIB, specifically labeled at the α-position of glutamine-11 with15N, was achieved by the Fmoc/tert.-butyl strategy in solution using a fragment condensation approach. Three fragments of zervamicin IIB were obtained by stepwise elongation with Fmoc amino acids using BOP as a coupling reagent. For the introduction of the highly sterically hindered α-aminoisobutyric acid residues, BOP/DMAP activation was applied. Peptide fragments were coupled by means of the coupling reagent, CF3-PyBOP. Using the strategy developed, zervamicin IIB specifically15N labeled has been synthesized in 30% overall yield based on the isotopically labeled amino acid. From 600 MHz NMR spectroscopy the position of the15N-label was clearly detected. The isotope enrichment (98 ±2%) was determined by FAB-mass spectrometry.
Key wordsantibiotic isotope labeling peptaibol peptide synthesis
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