Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 10, Issue 7, Pages 1607-1615Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200305571
Keywords
beta-peptides; electrostatic interactions; helical structures; NMR spectroscopy; salt bridges
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Two different strategies have been employed for the synthesis of Fmoc-protected beta(3)-homoarginine; the Arndt-Eistert homologation of alpha-arginine and the guanidinylation of beta(3)-homoornithine. Solid-phase beta-peptide synthesis was used for the preparation of beta-heptapeptide 1, which was de- signed to form a helix stabilized by electrostatic interactions through positively (beta(3)hArg) and negatively charged (beta(3)hGlu) amino acid residues. CD measurements and corresponding NMR investigations in MeOH and aqueous solutions do indeed show that the beta-peptidic 3(14)-helix can be stabilized by salt-bridge formation.
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