Letters in Peptide Science

, Volume 5, Issue 2–3, pp 175–178 | Cite as

Synthesis of the15N-Gln11 labeled peptaibol antibiotic zervamicin-IIB

  • Andrei Ogrel
  • Alexei Ogrel
  • Svetlana Ogrel
  • Vitaliy Shvets
  • Jan Raap
Article
  • 34 Downloads

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.

Key words

antibiotic isotope labeling peptaibol peptide synthesis 

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References

  1. 1.
    Ogrel, Al., Bloemhoff, W., Lugtenburg, J. and Raap, J., J. Pept. Sci. 3 (1997) 193.PubMedCrossRefGoogle Scholar
  2. 2.
    Egorova-Zachernyuk T., Shvets, V., Versluis, K., Heerma, W., Creemers, A., Nieuwenhuis, S., Lugtenburg, J., and Raap, J., J. Pept. Sci. 2 (1996) 341.PubMedCrossRefGoogle Scholar
  3. 3.
    Ogrel, Al., Bloemhoff, W, Lugtenburg, J. and Raap J., Liebigs Ann./Recueil. (1997) 41.Google Scholar
  4. 4.
    Lanzilotti, A., Littell, R., Fanshawe, W., McKenzie, T. and Lovell, M., J. Org. Chem., 44 (1979) 4809.CrossRefGoogle Scholar
  5. 5.
    Pearson, D., Blanchette, M., Baker, M. and Guindon, C., Tetrahedron Lett., 30 (1987) 2739.CrossRefGoogle Scholar
  6. 6.
    Wijkmans, J., Krujitzer, J., van der Marel, G., van Boom, J. and Bloemhoff, W., Recl. Trav. Chim. Pays-Bas., 113 (1994) 394.Google Scholar

Copyright information

© Kluwer Academic Publishers 1998

Authors and Affiliations

  • Andrei Ogrel
    • 1
  • Alexei Ogrel
    • 2
  • Svetlana Ogrel
    • 1
  • Vitaliy Shvets
    • 2
  • Jan Raap
    • 2
  1. 1.M.V. Lomonosov State Academy of Fine Chemical TechnologyMoscowRussia
  2. 2.Leiden Institute of ChemistryLeiden Universitythe Netherlands

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