Readily available chromenone receptors for carboxylates

Raposo, César; Crego, Mercedes; Mussons, Ma Luisa; Caballero, Ma Cruz; Morán, Joaquı́n R.

doi:10.1016/s0040-4039(00)76921-8

Cited by 29 publications

(14 citation statements)

References 5 publications

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“…responses to salicylate and perchlorate). This is consistent with the predicted favorable interaction of the carboxylate group of this anion with the ionophore from CPK models 3 Potentiometric responses of an o -NPOE-plasticized membrane containing 1 wt % ionophore 1 and 50 mol % TDMAC (relative to the ionophore) in 0.0100 M HEPES−NaOH pH 7.0: (1) sulfate, (2) chloride, (3) bromide, (4) nitrate, (5) iodide, (6) thiocyanate, (7) perchlorate, and (8) salicylate. …”

Section: Resultssupporting

confidence: 83%

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Tripodal Ionophore with Sulfate Recognition Properties for Anion-Selective Electrodes

et al. 2000

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Ionophore topology has a profound effect on the behavior of ion-selective electrodes. This is demonstrated with a new class of ionophores that incorporates aminochromenone moieties linked through urea spacers to different scaffolds that preorganize the ionophore binding cleft into tripodal topologies. Tris(2-aminoethylamine) and cis-1,3,5-tris(aminomethyl)cyclohexane were employed as the scaffolds. The two differ in their rigidity and in the size of ionophore cavity that they create. The electrodes based on the ionophore that incorporates the tris(2-aminoethylamine) scaffold show anti-Hofmeister behavior with an improved selectivity for sulfate. In contrast, the ionophore with the cis-1,3,5-tris(aminomethyl)cyclohexane scaffold exhibits a more Hofmeister-like response.

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Section: Resultssupporting

confidence: 83%

“…Details on the synthesis of the different ionophores can be found in refs −28. The synthesis of ionophore 1 is analogous to the one described in ref , with the exception of the starting material: a 6-bromochromene derivative was used in that reference, whereas for ionophore 1 , a 6- tert -butylchromene was used instead.…”

Section: Methodsmentioning

confidence: 99%

Tripodal Ionophore with Sulfate Recognition Properties for Anion-Selective Electrodes

et al. 2000

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“…The acidity of the ammonium salt may be enhanced by the introduction of a cocatalyst such as an aryl thiourea derivative, which has the ability to form a dual hydrogen bond with the carboxylate and the alkoxy group of the ammonium salt [42–44]. To ensure our postulation, a 1 H NMR spectroscopic study was carried out with a mixture of glycosyl acceptor 2a , pyridinium salt 3a (10 mol %) and aryl thiourea 4 (10 mol %) in CD 2 Cl 2 at room temperature (Fig.…”

Section: Resultsmentioning

confidence: 99%

Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors

Shaw

Kumar

Thakur

2017

Beilstein J. Org. Chem.

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The glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1,2-addition of alcohol to the electron-deficient pyridinium salt is increased in the presence of an aryl thiourea derivative as an hydrogen-bonding cocatalyst. This transformation occurs under mild reaction conditions with a wide range of O-glycosyl trichloroacetimidate donors and glycosyl acceptors to afford the corresponding O-glycosides in moderate to good yields with predictable selectivity. In addition, the optimized method is also utilized for the regioselective O-glycosylation by using a partially protected acceptor.

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“…As seen in Figure , the simplest is 3 and 4 , pioneered by Hamilton and co-workers in the context of receptors for barbiturates, and extended to hosts for quinone, diamides, and urea 16 and a variety of other applications . More rigid analogues of 3 and 4 that provide a similar spatial arrangement of two NH groups are seen in Morán's chromenone-based receptors 5 ( 6 ), our dimethylacetamide complexing tecton 7 , and Thummel's urea binder 8 . Integrating a highly preorganized unit such as 6 − 8 into a receptor such as 1 would represent a significant synthetic challenge, but there was interest in the quinoline analogue of 1 .…”

Section: Resultsmentioning

confidence: 99%

Structure−Function Studies on a Synthetic Guanosine Receptor That Simultaneously Binds Watson−Crick and Hoogsteen Sites

Quinn

Zimmerman

2005

J. Org. Chem.

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[structure: see text] A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via 1H NMR complexation studies in 5% DMSO-d6-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure-function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.

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Readily available chromenone receptors for carboxylates

Cited by 29 publications

References 5 publications

Tripodal Ionophore with Sulfate Recognition Properties for Anion-Selective Electrodes

Tripodal Ionophore with Sulfate Recognition Properties for Anion-Selective Electrodes

Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors

Structure−Function Studies on a Synthetic Guanosine Receptor That Simultaneously Binds Watson−Crick and Hoogsteen Sites

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