233661-54-6Relevant articles and documents
Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide
Fujimura, Futoshi,Fukuda, Makoto,Sugiyama, Junji,Morita, Tomoyuki,Kimura, Shunsaku
, p. 1896 - 1901 (2008/09/18)
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
Structure - Activity studies of 14-helical antimicrobial β-peptides: Probing the relationship between conformational stability and antimicrobial potency
Raguse, Tami L.,Porter, Emilie A.,Weisblum, Bernard,Gellman, Samuel H.
, p. 12774 - 12785 (2007/10/03)
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
Enantiomerically pure β-amino acids: A convenient access to both enantiomers of trans-2-aminocyclohexanecarboxylic acid
Berkessel, Albrecht,Glaubitz, Katja,Lex, Johann
, p. 2948 - 2952 (2007/10/03)
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.
Synthesis and characterization of trans-2-aminocyclohexanecarboxylic acid oligomers: An unnatural helical secondary structure and implications for β-peptide tertiary structure
Appella, Daniel H.,Christianson, Laurie A.,Karle, Isabella L.,Powell, Douglas R.,Gellman, Samuel H.
, p. 6206 - 6212 (2007/10/03)
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
