cis-2-Aminocyclopentanecarboxylic Acid Oligomers Adopt a Sheetlike Structure: Switch from Helix to Nonpolar Strand

Abstract

Rational control over helix and strand secondary structures is possible when conformationally restricted cyclic β‐amino acid residues are incorporated in the β‐peptides. Inversion of the relative configuration of these residues enables the preferred periodic structure to be switched from a helix to a single nonpolar strand (see picture).

A Novel Strategy Towards the Asymmetric Synthesis of Orthogonally Funtionalised 2-N-Benzyl-N-α-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.

“…The asymmetric synthesis of polyfunctionalised cyclopentane derivatives has been widely pursued in organic synthesis, with much recent interest focusing around strategies for the asymmetric synthesis of cis-pentacin (1) and trans-pentacin (2), respectively. The cis-diastereoisomer shows potent antifungal activity while Fülop et al have recently demonstrated that oligomers of cis-pentacin adopt a sheet type structure in DMSO [1].…”

“…The cis-diastereoisomer shows potent antifungal activity while Fülop et al have recently demonstrated that oligomers of cis-pentacin adopt a sheet type structure in DMSO [1]. Furthermore, Gellman et al have demonstrated that short chain β-peptides derived from trans-pentacin adopt 12-membered helical structures [2][3][4][5] and when a pyrrolidine-base β-amino acid is incorporated into the hexa-β-peptide 3, it confers water solubility when the ring nitrogen is protonated [6][7].…”

Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives

“…[18][19][20] Conformational studies of β-amino acid oligomers are also currently at the focus of interest. [21][22][23][24] Besides their diverse chemical compositions, β-amino acids and their derivatives possess noteworthy pharmacological effects; for example, (1R,2S)-2-aminocyclopentanecarboxylic acid (cispentacin) and some other alicyclic β-amino acids have marked antifungal activity. 25 The present work describes a mild and efficient ring opening of monoterpene-fused β-lactam enantiomers derived from (+)-and (-)-α-pinene, to produce a novel chiral β-amino acid and its derivatives.…”

Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid

“…6 cis-2-aminocyclopentanecarboxylic acid oligomers were later shown to be unnatural foldamers more suitable for rational design of new peptides showing novel tertiary structures, because they can adopt sheet like structures by switching from helix to nonpolar strands. 7 Several methods have been described for the synthesis of cyclopentane b-amino acids. 1c However, very few syntheses of polyhydroxylated derivatives have been reported.…”