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Guanidinium-Based Receptors for Oxoanions

Molecular Recognition

  1. Matthew P. Conley,
  2. Julián Valero,
  3. Javier de Mendoza

Published Online: 15 MAR 2012

DOI: 10.1002/9780470661345.smc061

Supramolecular Chemistry: From Molecules to Nanomaterials

Supramolecular Chemistry: From Molecules to Nanomaterials

How to Cite

Conley, M. P., Valero, J. and de Mendoza, J. 2012. Guanidinium-Based Receptors for Oxoanions. Supramolecular Chemistry: From Molecules to Nanomaterials. .

Author Information

  1. Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain

Publication History

  1. Published Online: 15 MAR 2012

Abstract

Nature frequently uses guanidinium–anion interactions for stabilization of protein structure or for catalytic reactivity in enzyme active sites. Studies of artificial guanidinium receptors show that strong hydrogen-bonded ion pairs with oxoanion substrates are formed in apolar media. This property has been used for the efficient extraction or membrane transport of racemic amino acids to give enantio-enriched products. However, inclusion of additional hydrogen-bond donors, or guanidinium functionalities, in the receptor molecule can stabilize the ion-pair interaction in polar protic solvents, allowing the detection of oxoanions near biologically relevant conditions. This approach has been used to recognize simple carboxylates and complex structures, such as proteins and DNA, in buffered water. Recent examples of catalysts containing guanidiniums show that this exceptional functional group can give both cooperative and regioselective reactivity to the system.

Keywords:

  • guanidinium;
  • hydrogen bonding;
  • ion pairing;
  • chiral recognition