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Journal article

The 'azirine/oxazolone method' in peptaibol synthesis: preparation of a derivative of trichotoxin A-50 (G).

  • 2007-06-26
Published in:
  • Chemistry & biodiversity. - 2007
Anti-Bacterial Agents
Antimicrobial Cationic Peptides
Azirines
Crystallography, X-Ray
Hydrolysis
Oxazolone
Peptides
English The synthesis of a mixture of epimeric derivatives of the peptaibol trichotoxin A-50 (G) is described. The 'azirine/oxazolone method' has been used as a superior method for the introduction of the Aib as well as the Iva units into the peptide chain. In this protocol, 2,2-disubstituted 2H-azirin-3-amines are the synthons for 2,2-disubstituted glycines, which undergo coupling with N-protected amino or peptide acids in high yield, and without any need of coupling reagents. The problem of the instability of the amide function of the Gln side chain under the conditions of the acid-catalyzed hydrolysis of Z-Gln-(Aib)(n)-N(Me)Ph was solved by using an appropriate protecting group for the amide function of the Gln side chain, e.g., the triphenylmethyl (trityl; Tr) group. The structures of two intermediate peptides, i.e., the segments comprising residues 1-5 and 10-13, resp., were established by X-ray crystallography.
Language
  • English
Open access status
green
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Persistent URL
https://susi.usi.ch/global/documents/219369
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