2011
DOI: 10.1021/ol201840p
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Synthesis and Structural Investigations of Functionalizable Hybrid β-Hairpin

Abstract: The solution and solid state conformations of a designed β-hairpin containing functionalizable α,β-unsaturated γ-amino acids at the antiparallel β-strands and a single step transformation to its saturated γ-peptide analogue are studied.

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Cited by 17 publications
(18 citation statements)
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“…We have been interested in the utilization of naturally occurring functionalized γ-amino acids such as statines 6 and α, β-unsaturated γ-amino acids 7 in the design of foldamers. We recently showed a stable β-hairpin 8 and unusual planar structures in hybrid peptides containing αand E-vinylogous amino acids. 9 We foreseen that the exceptional conformational properties of E-vinylogous amino acids can be explored to design highly organized protein supersecondary structure mimetics beyond the conventional secondary structures (helix, β-sheets and turns).…”
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confidence: 99%
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“…We have been interested in the utilization of naturally occurring functionalized γ-amino acids such as statines 6 and α, β-unsaturated γ-amino acids 7 in the design of foldamers. We recently showed a stable β-hairpin 8 and unusual planar structures in hybrid peptides containing αand E-vinylogous amino acids. 9 We foreseen that the exceptional conformational properties of E-vinylogous amino acids can be explored to design highly organized protein supersecondary structure mimetics beyond the conventional secondary structures (helix, β-sheets and turns).…”
mentioning
confidence: 99%
“…We postulated that Scheme 1: Synthesis of P1 (Boc-Leu-Aib-dγF-Leu-Aib-dγF-OEt) and P2 (Boc-Leu-Aib-dγA-Leu-Aib-dγA-OEt). the β-sheet promoting 10,8 and turn 11 inducing properties of Evinylogous amino acids can be readily exploited in the design of miniature β-meander mimetics. The β-meander is a common protein supersecondary structural motif consists of two or more anti-parallel β-strands and each adjacent strand are connected by β-turns.…”
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“…Recently, we reported the utility of E-vinylogous amino acids in the construction of a stable and functionalizable hybrid b-hairpin and its direct transformation to the g-peptide analogue. 6 We adopted a similar strategy for the synthesis of a/g 4 -hybrid peptides (Scheme 1). To understand the conformational properties of hybrid peptides with 1 : 1 alternating aand g 4 -amino acids, the a/E-vinylogous hybrid peptide Boc-Aib-dgF-Leu-dgF-OEt (D1) (dgF = a,b-unsaturated g-phenyl alanine) was synthesized in solution-phase using Boc-chemistry.…”
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confidence: 99%
“…En este grupo se encuentran especies que pueden colonizar además ambientes extremos como los ecosistemas hipersalinos, las fuentes termales o la nieve, posee también representantes de distribución cosmopolita con una elevada plasticidad adaptativa (Whitton & Potts, 2000); algunas especies pueden formar asociaciones con plantas y animales, mientras que otras tienen la capacidad de fijar nitrógeno molecular, lo que ayuda a la fertilización del suelo y al enriquecimiento de la columna de agua en el caso de las especies marinas. En esta clase se pueden encontrar especies de un gran potencial económico que producen metabolitos secundarios de un gran valor económico utilizados como agentes terapéuticos (Linington et al 2009;Tripathi et al 2010) de control biológico (Soltani et al 2005;Mian et al 2003) y como base para la síntesis de moléculas más complejas (Conroy et al 2010;Bandyopadhyay et al 2011) y pigmentos accesorios que son de alto valor agregado.…”
Section: Introductionunclassified