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Total Syntheses in Solution of TOAC‐Labelled Alamethicin F50/5 Analogues
Author(s) -
Peggion Cristina,
Jost Micha,
Baldini Chiara,
Formaggio Fernando,
Toniolo Claudio
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790104
Subject(s) - alamethicin , chemistry , residue (chemistry) , stereochemistry , amino acid , amino acid residue , peptide sequence , membrane , biochemistry , lipid bilayer , gene
Total syntheses in solution of a set of four selected analogues of the 19‐mer component F50/5 of alamethicin, the most extensively studied among the channel‐former peptaibol antibiotics, are planned and reported. All analogues bear three Glu(OMe) residues, replacing the Gln residues at positions 7, 18, and 19 of the naturally occurring compound. Three analogues are mono‐labelled with the free‐radical‐containing amino acid residue TOAC at the strategic positions 1, 8, or 16. The fourth analogue is bis‐labelled with the same EPR‐active residue at both positions 1 and 16. In the native sequence, all of the positions where TOAC replacements have been introduced are characterized by residues of Aib, the prototype of the class of helicogenic C α ‐tetrasubstituted α ‐amino acids. All of the TOAC analogues synthesized exhibit significant membrane‐modifying properties.