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  • Title: Self-assembling of the porphyrin-linked acyclic penta- and heptapeptides in aqueous trifluoroethanol.
    Author: Arai T, Inudo M, Ishimatsu T, Akamatsu C, Tokusaki Y, Sasaki T, Nishino N.
    Journal: J Org Chem; 2003 Jul 11; 68(14):5540-9. PubMed ID: 12839445.
    Abstract:
    The conjugates of porphyrin with links to the acyclic penta- and heptapeptides were synthesized to mimic natural multiple porphyrin systems. The linear penta- and heptapeptide with hydrophilic/hydrophobic alternative sequences took a random structure in aqueous trifluoroethanol (TFE). However, these polypeptides took a beta-sheet structure in the same solvent when the N-terminal Cys linked to the porphyrin, suggesting that the conjugates self-assembled via the intermolecular hydrophobic interaction between the porphyrins. The circular dichroism (CD) spectra, UV/vis spectra, size exclusion chromatography (SEC), and (1)H NMR spectroscopy supported the self-assembling. In the self-assembled structure of the pentapeptide linking porphyrin at the p-phenyl position (9), the porphyrins were involved in two porphyrin-porphyrin interactions, i.e., the side-by-side interaction between the neighboring polypeptide chains and the face-to-face interaction between the first and the third peptide chains. The CD spectra of 9 showed two sets of Cotton effects probably arising from these two interactions. The UV/vis spectra also supported the above interpretation, showing multiple absorptions in the longwave and shortwave shifted regions. The SEC analyses showed the assembled structure of the conjugates. The (1)H NMR signals of the porphyrin rings of 9 were hardly observed in D(2)O-CD(3)OD because of the shortened spin-spin relaxation time T(2)().
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