Enantiomer recognition of organic ammonium salts by podand- and crown-type monensin amides: new synthetic strategy for chiral receptors

Maruyama, Kazuhiro; Sohmiya, Hajime; Tsukube, Hiroshi

doi:10.1016/s0040-4020(01)88185-0

Cited by 31 publications

(30 citation statements)

References 42 publications

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“…As demonstrated by experiments in an ion selective electrode in buffered aqueous solution and by NMR studies in chloroform, enantioselective complexation is found for chiral phenethylamine and naphthylamine salts, as well as for some amino acid esters. ( R )-1-(l-Naphthyl)ethylammonium acetate is bound with three fold selectivity over the corresponding S -enantiomer by ( S )- 224b [ 714 ].…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

213

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.

213

130

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“…amino acid esters. 31 Naturally-occurring fluorescent siderophores such as azotobactin d (a pyoverdin type siderophore) as well as fluorescentlabeled non-fluorescent siderophores such as desferrioxamine have been employed for the fluorometric detection of Fe(III). 32 The ferric-siderophore complexes interact with specific bacterial cell membrane receptors with association constants of up to 10 8 -10 9 M À1 , providing a possibility for detection of pathogens.…”

Section: Natural Compounds As Hostsmentioning

confidence: 99%

Supramolecular complexations of natural products

Schneider

Agrawal²,

Yatsimirsky

2013

Chem. Soc. Rev.

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Complexations of natural products with synthetic receptors as well as the use of natural products as host compounds are reviewed, with an emphasis on possible practical uses or on biomedical significance. Applications such as separation, sensing, enzyme monitoring, and protection of natural drugs are first outlined. We then discuss examples of complexes with all important classes of natural compounds, such as amino acids, peptides, nucleosides/nucleotides, carbohydrates, catecholamines, flavonoids, terpenoids/steroids, alkaloids, antibiotics and toxins.

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“…Membranes with different CD derivatives and different plasticizers have been investigated, and the best results have been obtained for PVC membrane containing per-(MetO)b-CD and bis(2-ethhylhexyl) sebacate (DOS) as plasticizer. The potentiometric response of membrane ion-selective electrodes with antibiotic monensin used as ionophore to enantiomers of phenylalanine methyl ester cations (Maruyama et al 1992). The selectivity coefficient calculated for response of membrane containing per-(MetO)-b-CD and bis(2-ethhylhexyl) sebacate as plasticizer in measurements conditioned in individual enantiomers was log K pot ¼ 2 2.11, whereas for the membrane containing per-(MeO)-b-CD, o-NPOE, PVC, KTpClB and conditioned in S enantiomer and successive Figure 1.…”

Section: Enantioselective Sensors and Biosensorsmentioning

confidence: 99%

Electrochemical and Piezoelectric Enantioselective Sensors and Biosensors

Trojanowicz

Wcisło

2005

Analytical Letters

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Enantioselectivity in chemical and biochemical sensing probes can be obtained by the use of enantioselective binding or by enantioselective biocatalysis. The enantioseletive discrimination in ion-selective electrodes can be achieved with the use of appropriate ionophore in plasticized membrane in measuring cell or on the surface of electrode, with the use of a suitable enzyme in biosensor, antibody in immunosensor, or molecularly imprinted polymer for modification of active surface of amperometric or voltammetric sensor. This review, based on 77 literature references mostly from 1992 to 2004, reports developments of such sensors for potentiometric, amperometric, and mass-detecting devices involving quartz crystal microbalances. for allowing MW to have study visits in their laboratories to get experimental experience in fabrication of potentiometric sensors and amperometric biosensors.

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Enantiomer recognition of organic ammonium salts by podand- and crown-type monensin amides: new synthetic strategy for chiral receptors

Cited by 31 publications

References 42 publications

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Supramolecular complexations of natural products

Electrochemical and Piezoelectric Enantioselective Sensors and Biosensors

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