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Formation of gels in the presence of metal ions

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Abstract

A small library of stereoisomeric pseudopeptides able to make gels in different solvents has been prepared and their attitude to make gels in the presence of several metal ions was evaluated. Four benzyl esters and four carboxylic acids, all containing a moiety of azelaic acid (a long chain dicarboxylic acid) coupled with four different pseudopeptide moieties sharing the same skeleton (a phenyl group one atom apart from the oxazolidin-2-one carboxylic group), were synthesized in solution, by standard coupling reaction. The tendency of these pseudopeptides to form gels was evaluated using the inversion test of 10 mM solutions of pure compounds and of stoichiometric mixtures of pseudopeptides and metal ions. To obtain additional information on the molecular association, the gel samples were left dry in the air to form xerogels that were further analyzed using SEM and XRD. The formation of gel containing Zn(II) or Cu(II) ions gave good results in term of incorporation of the metal ions, while the presence of Cu(I), Al(III) and Mg(II) gave less satisfactory results. This outcome is a first insight in the formation of stable LMWGs formed by stoichiometric mixtures of pseudopeptides and metal ions. Further studies will be carried out to develop similar compounds of pharmacological interest.

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Scheme 1
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Abbreviations

d-Oxd:

(4R,5S)-4-Carboxy-5-methyl oxazolidin-2-one

LMWG:

Low molecular-weight gelator

l-Phe:

l-Phenylalanine

SEM:

Scanning electron microscopy

XRD:

X-ray powder diffraction

CH2Cl2 :

Dichloromethane

AcOEt:

Ethyl acetate

MeOH:

Methanol

αMe-Phg:

β3-Homophenylglycine

β3-hPhg:

α-Methyl-phenylglycine

OBn:

O-Benzyl

d-Pro:

d-Proline

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Acknowledgments

CT is grateful to Ministero dell’Università e della Ricerca Scientifica (PRIN 2008), Università di Bologna (Funds for selected topics) and to Fondazione del Monte di Bologna e di Ravenna for financial support. GF thanks the Consorzio Inter-Universitario di Ricerca della Chimica dei Metalli nei Sistemi Biologici for financial support.

Conflict of interest

The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Dipartimento di Chimica “G. Ciamician”, Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126, Bologna, Italy

    Nicola Castellucci, Giuseppe Falini & Claudia Tomasini

  2. Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland

    Gaetano Angelici

Authors
  1. Nicola Castellucci
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  2. Giuseppe Falini
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  3. Gaetano Angelici
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  4. Claudia Tomasini
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Correspondence to Claudia Tomasini.

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Castellucci, N., Falini, G., Angelici, G. et al. Formation of gels in the presence of metal ions. Amino Acids 41, 609–620 (2011). https://doi.org/10.1007/s00726-011-0908-0

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  • DOI: https://doi.org/10.1007/s00726-011-0908-0

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