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Paper | Regular issue | Vol 65, No. 10, 2005, pp.2395-2409
Published online, 23rd August, 2005
DOI: 10.3987/COM-05-10490
1,3-Benzodioxole-based β- and γ-Peptide Linkages Exhibiting Unique Fluorescence, Conformation, and Self-association Properties

Masaya Suzuki, Yuya Ohguro, Kazukiyo Kobayashi, and Yoshihiro Nishida*

*Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan

Abstract

Four types of β- and γ-peptide models were prepared from our previous asymmetric 1,3-benzodioxole and characterized by means of fluorescence and 1H NMR spectroscopy. A β-peptide model carrying secondary amide linkages at both of the C- and N-termini took a rigid coplanar conformation, emitting the strongest fluorescence [Ex.(max) 340 nm and Em.(max) 424 nm] among the four models. Dual intra-molecular hydrogen bonds were associated with the stable coplanar conformation. A tertiary β-peptide model carrying a tertiary amide linkage at the C-terminus took a twisted conformation around the C-terminal to afford a pair of rotational isomers (atropisomers) detectable with 1H NMR spectroscopy. Both secondary and tertiary γ-peptide models showed a notable self-association property to afford dimers made of complementary intra- and intermolecular hydrogen bonds.