Complexation of basic amino acids by water-soluble calixarene sulphonates as a study of the possiblemechanisms of recognition of calixarene sulphonates by proteins

Douteau‐Guével, Nathalie; Coleman, Anthony W.; Morel, Jean‐Pierre; Morel‐Desrosiers, Nicole

doi:10.1002/(sici)1099-1395(1998100)11:10<693::aid-poc18>3.0.co;2-8

Cited by 88 publications

(15 citation statements)

References 22 publications

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“…The affinity of the p -sulfonatocalix[ n ]arenes ( 84 ) ( n = 4, 6, and 8) towards amino acids was also extensively investigated by 1 H NMR [290–292], microcalorimetry [293] and HPLC-methods [294]. …”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

203

130

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SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

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Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

203

130

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“…Owing to their high water solubility (> 0.1 M) and low toxicity, SCn macrocycles have been widely investigated for their pharmaceutical and biological applications [21,[68][69][70][71][72][73][74]. In early studies by Douteau-Guével et al and Selkti et al the complexation of p-sulfonatocalix[n]arene (n = 4, 6 and 8) with Lys and Arg was explored by NMR spectroscopy and microcalorimetry in solution and by X-ray diffraction in the solid state [21,75,76]. The 1 H NMR studies carried out at different pH values showed that the calixarenes do not interact with these amino acids at pH 13 due to the deprotonation of the amino and guanidino groups, this last one being only partially deprotonated under these conditions (pKa = 13.2) [75].…”

Section: P-sulfonatocalix[n]arenesmentioning

confidence: 99%

“…SC4 was investigated in more detail at pH 1 and 5, showing that the receptor displays higher affinity for both amino acids at pH 5 and that, independently of the pH, Arg (K = 1.7 × 10 3 M −1 at pH 5, K = 2.0 × 10 2 M −1 at pH 1) binds more strongly than Lys (K = 6.0 × 10 2 In early studies by Douteau-Guével et al and Selkti et al the complexation of psulfonatocalix[n]arene (n = 4, 6 and 8) with Lys and Arg was explored by NMR spectroscopy and microcalorimetry in solution and by X-ray diffraction in the solid state [21,75,76]. The 1 H NMR studies carried out at different pH values showed that the calixarenes do not interact with these amino acids at pH 13 due to the deprotonation of the amino and guanidino groups, this last one being only partially deprotonated under these conditions (pK a = 13.2) [75]. At more acidic pH conditions (pH 5 and pH 1), the authors also pointed out the weaker interactions between these amino acids and the larger SC6 and SC8 hosts, attributing the low affinity to the more flexible structure of these hosts.…”

Section: P-sulfonatocalix[n]arenesmentioning

confidence: 99%

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

2020

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To this day, the recognition and high affinity binding of biomolecules in water by synthetic receptors remains challenging, while the necessity for systems for their sensing, transport and modulation persists. This problematic is prevalent for the recognition of peptides, which not only have key roles in many biochemical pathways, as well as having pharmacological and biotechnological applications, but also frequently serve as models for the study of proteins. Taking inspiration in nature and on the interactions that occur between several receptors and peptide sequences, many researchers have developed and applied a variety of different synthetic receptors, as is the case of macrocyclic compounds, molecular imprinted polymers, organometallic cages, among others, to bind amino acids, small peptides and proteins. In this critical review, we present and discuss selected examples of synthetic receptors for amino acids and peptides, with a greater focus on supramolecular receptors, which show great promise for the selective recognition of these biomolecules in physiological conditions. We decided to focus preferentially on small synthetic receptors (leaving out of this review high molecular weight polymeric systems) for which more detailed and accurate molecular level information regarding the main structural and thermodynamic features of the receptor biomolecule assemblies is available.

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“…Furthermore, the nature of the pendants allows for subtle tuning of the polarity of both the down - and the external -regions, and the size of the up -region. The capability to discriminate biomolecules such as the zwitterionic forms of aromatic amino acids [12], basic amino acids [13–15], aliphatic and aromatic native amino acids [16–18], and amines and peptides [19], by acting as an artificial receptor [20–30], is thanks to this structural versatility.…”

Section: Reviewmentioning

confidence: 99%

Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system

Fraschetti¹,

Letzel²,

Filippi³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThis review describes the state-of-art in the field of the gas-phase reactivity of diastereomeric complexes formed between a chiral artificial receptor and a biologically active molecule. The presented experimental approach is a ligand-displacement reaction carried out in a nano ESI-FT-ICR instrument, supported by a thermodynamic MS-study and molecular-mechanics and molecular-dynamics (MM/MD) computational techniques. The noncovalent ion–molecule complexes are ideal for the study of chiral recognition in the absence of complicating solvent and counterion effects.

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Complexation of basic amino acids by water-soluble calixarene sulphonates as a study of the possiblemechanisms of recognition of calixarene sulphonates by proteins

Cited by 88 publications

References 22 publications

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Selective Recognition of Amino Acids and Peptides by Small Supramolecular Receptors

Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system

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