Enantioselective recognition of a chiral quaternary ammonium ion by C3 symmetric cyclic hexapeptides

Heinrichs, G.; Vial, Laurent; Lacour, Jérôme; Kubik, Stefan

doi:10.1039/b302092d

Cited by 35 publications

(15 citation statements)

References 14 publications

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“…In a second study it was shown, that these cyclic peptides show enantiodiscrimination properties [747]. The best two examples, 233e and 233f , distinguish the two enantiomers of N , N , N -trimethyl-1-phenylethyl ammonium picrate in 0.1% DMSO–CDCl 3 with K R /K S = 1.5.…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

219

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.

219

130

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“…Solutions of salts [Bu 3 NH][L-22] in CHCl 3 or [cinchonidinium][D-22] in 7.5-10% DMSO/CHCl 3 were prepared (1 equiv.) and added to orange-coloured solutions of racemic [55]Cl 2 or [57]Cl 2 in water (1 equiv.). Upon vigorous stirring of the biphasic mixtures, a partial transfer of coloration occurred from the aqueous layers to the organic ones (Fig.…”

Section: By Asymmetric Extractionmentioning

confidence: 99%

“…Ion pairing of this cation with racemic 22 improves the binding affinity in CHCl 3 by a factor of ~3 over picrate. 57 Fontecave and co-workers have been able to resolve the cis-[Ru(dmp) 2 (CH3CN) 2 ] complex (dmp = 2,9-dimethyl-1,10-phenanthroline) using D-22 as counterions. This "chiralat-metal" ruthenium derivative was then used as a catalyst for the oxidation of sulfides to sulfoxides by hydrogen peroxide.…”

Section: Addendummentioning

confidence: 99%

Recent developments in chiral anion mediated asymmetric chemistry

2003

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“…[1,2] Concave receptor structures with rigidly oriented or conformationally locked functional groups are therefore among the most potent systems for molecular recognition. [3][4][5][6][7][8][9][10][11][12][13][14] Since many target molecules for sensors exhibit C 3 or pseudo-C 3 symmetry, complementary scaffolds with threefold symmetry are popular. [15] An unusual large and rigid backbone providing concave and convergent preorganized functional groups for supramolecular interaction was established by us recently.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Rigid Receptors Based on Triphenylene Ketals

et al. 2005

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The synthesis of rigid receptors based on triphenylene ketals, including some improved procedures, is described in detail. Since chemical transformations are strongly influenced by the rigid character and steric bulkiness of the receptors, the construction of a subunit allowing quicker synthetic development is also reported. The preparation of these receptor structures involves an oxidative trimerization and a subsequent repeated isomerization procedure. The scope for the attachment of sterically demanding affinity groups on the receptor scaffold and the corresponding subunit is discussed, and the molecular structures and available space for molecular recognition of the chirally modified systems are outlined by some crystal structures. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Enantioselective recognition of a chiral quaternary ammonium ion by C3 symmetric cyclic hexapeptides

Abstract: C3 Symmetric cyclic hexapeptides containing alternating L-proline and 3-aminobenzoic acid derivatives as subunits possess different affinities towards the two enantiomers of the N,N,N-trimethyl-1-phenylethyl ammonium cation.

Cited by 35 publications

References 14 publications

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Recent developments in chiral anion mediated asymmetric chemistry

Synthesis of Rigid Receptors Based on Triphenylene Ketals

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