- Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide
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A novel cyclic trimer of a β-amino acid, trans-2- aminocyclohexylcarboxylic acid, was synthesized and its conformation and ability to form assemblies investigated. FT-IR and NMR measurements and computational calculations showed that this cyclic tri-β-pep
- Fujimura, Futoshi,Fukuda, Makoto,Sugiyama, Junji,Morita, Tomoyuki,Kimura, Shunsaku
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p. 1896 - 1901
(2008/09/18)
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- Structure - Activity studies of 14-helical antimicrobial β-peptides: Probing the relationship between conformational stability and antimicrobial potency
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Antimicrobial α-helical α-peptides are part of the host-defense mechanism of multicellular organisms and could find therapeutic use against bacteria that are resistant to conventional antibiotics. Recent work from Hamuro et al. has shown that oligomers of
- Raguse, Tami L.,Porter, Emilie A.,Weisblum, Bernard,Gellman, Samuel H.
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p. 12774 - 12785
(2007/10/03)
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- Enantiomerically pure β-amino acids: A convenient access to both enantiomers of trans-2-aminocyclohexanecarboxylic acid
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Enantiomerically pure trans-2-aminocyclohexanecarboxylic acid is an important building block for helical β-peptides. We report here that this amino acid can be obtained from trans-cyclohexane-1,2-dicarboxylic acid in good yield by a simple one-pot procedure comprising cyclization to the anhydride, amide formation with ammonia, and a subsequent Hofmann-type degradation with phenyliodine(III) bis(trifluoroacetate) (PIFA) as the oxidant. The N-Fmoc- and N-BOC-protected derivatives were obtained by treatment of the amino acid with Fmoc-OSu and BOC2O, respectively. The N-BOC derivative could be prepared in even better overall yield by a one-pot procedure leading directly from trans-cyclohexane-1,2-dicarboxylic acid to the N-BOC-protected amino acid. Both enantiomers of the starting trans-1,2-cyclohexanedicarboxylic acid can be obtained easily and in large quantities by separating commercially available racemic trans-1,2-cyclohexanedicarboxylic acid using either (R)- or (S)-1-phenethylamine. X-ray crystallography of the diastereomerically pure salt obtained from (R)-1-phenethylamine revealed that the configuration of the diacid component is (1R,2R), and not (1S,2S) as reported in the literature. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Berkessel, Albrecht,Glaubitz, Katja,Lex, Johann
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p. 2948 - 2952
(2007/10/03)
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- Synthesis and characterization of trans-2-aminocyclohexanecarboxylic acid oligomers: An unnatural helical secondary structure and implications for β-peptide tertiary structure
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The preparation, crystal structures, and circular dichroism (CD) spectra of two oligomers of optically active trans-2-aminocyclohexanecarboxylic acid are reported. In the solid state, both the tetramer and the hexamer of this β-amino acid display a helica
- Appella, Daniel H.,Christianson, Laurie A.,Karle, Isabella L.,Powell, Douglas R.,Gellman, Samuel H.
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p. 6206 - 6212
(2007/10/03)
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