2010
DOI: 10.1039/b918755c
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Folding and self-assembling with β-oligomers based on (1R,2S)-2-aminocyclobutane-1-carboxylic acid

Abstract: Improved methodologies are provided to synthesize (1R,2S)-2-aminocyclobutane-1-carboxylic acid derivatives and their incorporation into beta-peptides of 2-8 residues bearing different N-protecting groups. The conformational analysis of these oligomers has been carried out by using experimental techniques along with theoretical calculations. This study shows that these oligomers adopt preferentially a strand-type conformation in solution induced by the formation of intra-residue six-membered hydrogen-bonded rin… Show more

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Cited by 61 publications
(60 citation statements)
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“…[21][22][23][24] Infinite pleated sheet aggregates were also observed, which eventually appeared in the form of nanostructured fibrils. [25][26][27][28][29] These processes are very similar to those leading to the formation of solvophobic interaction-driven tertiary/ quaternary structures observed for natural proteins. Although peptidic foldamers exhibit greatly increased diversity in the periodic secondary-structure space as compared with their natural counterparts, the question of whether these intriguing sequences are able to demonstrate modes of the largest-diameter β-peptidic mixed helix to date, the H18/20 P helix.…”
Section: Introductionmentioning
confidence: 60%
“…[21][22][23][24] Infinite pleated sheet aggregates were also observed, which eventually appeared in the form of nanostructured fibrils. [25][26][27][28][29] These processes are very similar to those leading to the formation of solvophobic interaction-driven tertiary/ quaternary structures observed for natural proteins. Although peptidic foldamers exhibit greatly increased diversity in the periodic secondary-structure space as compared with their natural counterparts, the question of whether these intriguing sequences are able to demonstrate modes of the largest-diameter β-peptidic mixed helix to date, the H18/20 P helix.…”
Section: Introductionmentioning
confidence: 60%
“…Alkaline hydrolysis of rac-13 gave direct access to the bicyclic amino acid rac-15 (72 %; Scheme 4, Path a). H 2 SO 4 , reflux; Scheme 5) [42,43] yielded the N-protected bicyclic dicarboxylic acid ester derivative 18 (60 %) with the configuration of the starting material unchanged. Subsequent treatment of rac-16 with an anion exchanger Merck III in MeOH allowed selective removal of the N-trifluoroacetyl moiety, providing, after workup with HCl, methyl ester rac-17a as the hydrochloride (79 %).…”
Section: Resultsmentioning
confidence: 99%
“…[3] Then on-typical conformational arrangements of b-peptides, as well as their other unique properties (e.g., high resistance against enzymatic hydrolysis), has led to the discovery of numerous molecules with valuable properties. [9] Moreover,o ther distinctive properties such as gelation, [10] catalysis, [11] self-organization, [12] and molecular recognition [13] have been shown for peptides containing b-amino acids. [9] Moreover,o ther distinctive properties such as gelation, [10] catalysis, [11] self-organization, [12] and molecular recognition [13] have been shown for peptides containing b-amino acids.…”
mentioning
confidence: 99%