Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by <i>C</i><sub>3</sub>‐Symmetric Peptide Receptors

Schnopp, Markus; Haberhauer, Gebhard

doi:10.1002/ejoc.200900510

Cited by 30 publications

(21 citation statements)

References 76 publications

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“…66,97,98 Lissoclinum-derived and other synthetic cyclic peptides have been used as platforms for applications in molecular recognition. 97,99 Synthetic C 2 and C 3 symmetric macrocycles (see Scheme 3) were prepared for the selective coordination of anions -where significant stabilities and selectivities were achieved and interpreted on the basis of DFT calculations, 83,98,100 the enantioselective coordination of chiral organo-ammonium ions with selectivities of up to 87 : 13, 101 and as a novel class of C 3 -symmetric cylindrical and conical container molecules, based on chiral glutamic acid and lysinederived thiazole amino acids (also given in Scheme 3).…”

Section: Dalton Transactions Perspectivementioning

confidence: 99%

Cyclic peptide marine metabolites and Cu^II

et al. 2014

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a Cyclic pseudo-peptides derived from marine metabolites of the genus Lissoclinum bistratum and Lissoclinum patella have attracted scientific interest in the last two decades. Their structural properties and solution dynamics have been analyzed in detail, elaborate synthetic procedures for the natural products and synthetic derivatives developed, the biosynthetic pathways studied and it now is possible to produce them biosynthetically. Initially, these macrocyclic ligands were studied due to their medicinal and pharmaceutical potential -some of the isolated cyclic pseudo-peptides show high cytotoxic and antiviral activity.A major focus in the last decade has been on their Cu II coordination chemistry, as a number of studies have indicated that dinuclear Cu II complexes of cyclic peptides may be involved in the ascidians' metabolism, and this is the focus of the present review.

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Section: Dalton Transactions Perspectivementioning

confidence: 99%

Cyclic peptide marine metabolites and Cu^II

et al. 2014

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“…128) that bind α-chiral primary organoammonium ions with up to 30,000 M –1 [572]. The binding constants and the selectivity ratios were estimated by standard 1 H NMR titration techniques in CDCl 3 .…”

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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“…Haberhauer et al [98] synthesized the C3-symmetric imidazole-containing macrocyclic peptide receptors, (251-253) (Scheme 44) with different binding arms. The simple using N-alkylation of known scaffold, 250 with the corresponding halogenomethylcompounds afforded the desired receptors.…”

Section: Chiral Selectors N-ac-amino Acid Tetrabutyl Ammonium Saltmentioning

confidence: 99%

Chiral Heterocycle-Based Receptors for Enantioselective Recognition

et al. 2018

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Abstract:The majority of biomolecules found in living beings are chiral, therefore chiral molecular recognition in living systems is crucial to life. Following Cram's seminal work on the crown-based chiral recognition, prominent research groups have reported innumerable chiral receptors with distinctly different geometrical features and asymmetry elements. Main applications of such chiral receptors are found in chiral chromatography, as for analytical purposes and for bulk separation of racemates.Incorporation of heterocyclic rings in these recognition systems added a new dimension to the existing group of receptors. Heterocycles have additional features such as availability of unshared electron pairs, pronounced conformational features, introduction of hydrogen bonding and presence of permanent dipoles as well as specific spectral properties in certain cases. These features are found to enhance binding properties of the receptors and the selectivity factors between opposite enantiomers, allowing them to be effectively separated. The review presents the synthetic approaches towards these heterocyclic receptors and their distinctly different behavior vis-à-vis carbocyclic receptors.

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Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C₃‐Symmetric Peptide Receptors

Cited by 30 publications

References 76 publications

Cyclic peptide marine metabolites and Cu^II

Cyclic peptide marine metabolites and Cu^II

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Chiral Heterocycle-Based Receptors for Enantioselective Recognition

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Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C3‐Symmetric Peptide Receptors

Cited by 30 publications

References 76 publications

Cyclic peptide marine metabolites and CuII

Cyclic peptide marine metabolites and CuII

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Chiral Heterocycle-Based Receptors for Enantioselective Recognition

Contact Info

Product

Resources

About

Highly Selective Recognition of α‐Chiral Primary Organoammonium Ions by C₃‐Symmetric Peptide Receptors

Cyclic peptide marine metabolites and Cu^II

Cyclic peptide marine metabolites and Cu^II