Summary
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.
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References
Ogrel, Al., Bloemhoff, W., Lugtenburg, J. and Raap, J., J. Pept. Sci. 3 (1997) 193.
Egorova-Zachernyuk T., Shvets, V., Versluis, K., Heerma, W., Creemers, A., Nieuwenhuis, S., Lugtenburg, J., and Raap, J., J. Pept. Sci. 2 (1996) 341.
Ogrel, Al., Bloemhoff, W, Lugtenburg, J. and Raap J., Liebigs Ann./Recueil. (1997) 41.
Lanzilotti, A., Littell, R., Fanshawe, W., McKenzie, T. and Lovell, M., J. Org. Chem., 44 (1979) 4809.
Pearson, D., Blanchette, M., Baker, M. and Guindon, C., Tetrahedron Lett., 30 (1987) 2739.
Wijkmans, J., Krujitzer, J., van der Marel, G., van Boom, J. and Bloemhoff, W., Recl. Trav. Chim. Pays-Bas., 113 (1994) 394.
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Ogrel, A., Ogrel, A., Ogrel, S. et al. Synthesis of the15N-Gln11 labeled peptaibol antibiotic zervamicin-IIB. Lett Pept Sci 5, 175–178 (1998). https://doi.org/10.1007/BF02443464
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DOI: https://doi.org/10.1007/BF02443464