Secondary structure of short β-peptides as the chiral expression of monomeric building units

A rational and predictive model

Esther Gorrea, Gábor Pohl, Pau Nolis, Sergio Celis, Kepa K. Burusco, Vicenç Branchadell, A. Perczel, Rosa M. Ortuño

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Chirality of the monomeric residues controls and determines the prevalent folding of small oligopeptides (from di- to tetramers) composed of 2-aminocyclobutane-1-carboxylic acid (ACBA) derivatives with the same or different absolute and relative configuration. The cis-form of the monomeric ACBA gives rise to two conformers, namely, Z6 and Z8, while the trans-form manifests uniquely as an H8 structure. By combining these subunits in oligo- and polypeptides, their local structural preference remains, thus allowing the rational design of new short foldamers. A lego-type molecular architecture evolves; the overall look depends only on the conformational properties of the structural building units. A versatile and efficient method to predict the backbone folds of designed cyclobutane β-peptides is based on QM calculations. Predictions are corroborated by high-resolution NMR studies on selected stereoisomers, most of them being new foldamers that have been synthesized and characterized for the first time. Thus, the chiral expression of monomeric building units results in the defined secondary structures of small oligomers. As a result of this study, a new set of chirality controlled foldamers is provided to probe as biocompatible biopolymers.

Original languageEnglish
Pages (from-to)9795-9806
Number of pages12
JournalJournal of Organic Chemistry
Volume77
Issue number21
DOIs
Publication statusPublished - Nov 2 2012

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Oligopeptides
Chirality
Cyclobutanes
Peptides
Biopolymers
Stereoisomerism
Oligomers
Nuclear magnetic resonance
Derivatives
2-aminocyclobutane-1-carboxylic acid
Z 008

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Gorrea, E., Pohl, G., Nolis, P., Celis, S., Burusco, K. K., Branchadell, V., ... Ortuño, R. M. (2012). Secondary structure of short β-peptides as the chiral expression of monomeric building units: A rational and predictive model. Journal of Organic Chemistry, 77(21), 9795-9806. https://doi.org/10.1021/jo302034b

Secondary structure of short β-peptides as the chiral expression of monomeric building units : A rational and predictive model. / Gorrea, Esther; Pohl, Gábor; Nolis, Pau; Celis, Sergio; Burusco, Kepa K.; Branchadell, Vicenç; Perczel, A.; Ortuño, Rosa M.

In: Journal of Organic Chemistry, Vol. 77, No. 21, 02.11.2012, p. 9795-9806.

Research output: Contribution to journalArticle

Gorrea, Esther ; Pohl, Gábor ; Nolis, Pau ; Celis, Sergio ; Burusco, Kepa K. ; Branchadell, Vicenç ; Perczel, A. ; Ortuño, Rosa M. / Secondary structure of short β-peptides as the chiral expression of monomeric building units : A rational and predictive model. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 21. pp. 9795-9806.
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