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Toward the rational design of molecular rotors ion sensors based on α,γ-cyclic peptide dimers

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Abstract

A dimer-forming self-assembling cyclic hexapeptide with a control register and a large association constant in water is described. The self-assembly process is followed by pyrene-excimer emission and the main diastereomeric dimer present in solution is switched by controlled addition of divalent cations (e.g., Ca, Mg) or oxalic acid.

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Scheme 1
Scheme 2
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Abbreviations

Acp:

3-Aminocyclopentanecarboxylic Acid

CPs:

Cyclic peptides

α,γ-D:

Dimer of a α,γ-cyclic peptide

DIEA:

Diisopropylethylamine

4-DPPBA:

4-(Diphenylphosphino)benzoic Acid

ext-TTF:

2-[9-(1,3-dithiol-2-ylidene)anthracen-10(9H)-ylidene]-1,3-dithiole

Pap:

5-(pyren-1-yl)pentanoic acid

PCBA:

[6,6]-phenyl-C61-butyric acid

SPN:

Self-assembling Peptide Nanotubes

TBAF:

Tetrabutylamonium chloride

TBTU:

O-Benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate

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Acknowledgments

This work was supported by the Spanish Ministry of Science and Innovation (MICINN) and the ERDF [SAF2007-61015, CTQ2007-68057-C02-01/BQU and Consolider Ingenio 2010 (CSD2007-00006)], the Xunta de Galicia (PGIDIT08CSA047209PR and GRC2010/012) and European project Magnifyco (NMP4-SL-2009-228622). MJPA thanks the Spanish MICINN for her PhD contract (FPI).

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Authors and Affiliations

  1. Departamento de Química Orgánica, Unidad Asociada al CSIC y Centro Singular de Investigación en Química Biológica y Materiales Moleculares, Universidad de Santiago de Compostela, Campus Vida, 15782, Santiago, Spain

    María Jesús Pérez-Alvite, Luis Castedo & Juan R. Granja

  2. Departamento de Química Física y Centro Singular de Investigación en Química Biológica y Materiales Moleculares, Universidad de Santiago de Compostela, Campus Vida, 15782, Santiago, Spain

    Manuel Mosquera

Authors
  1. María Jesús Pérez-Alvite
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  2. Manuel Mosquera
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  3. Luis Castedo
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  4. Juan R. Granja
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Corresponding author

Correspondence to Juan R. Granja.

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Pérez-Alvite, M.J., Mosquera, M., Castedo, L. et al. Toward the rational design of molecular rotors ion sensors based on α,γ-cyclic peptide dimers. Amino Acids 41, 621–628 (2011). https://doi.org/10.1007/s00726-011-0886-2

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