Highly Stereospecific Generation of Helical Chirality by Imprinting with Amino Acids: A Universal Sensor for Amino Acid Enantiopurity

Kim, Hyun Woo; So, Soon Mog; Yen, Cindy Pai-Hui; Vinhato, Elisângela; Lough, Alan J.; Hong, Jong‐In; Kim, Hae-Jo; Chin, Jik

doi:10.1002/anie.200803116

Cited by 98 publications

(33 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[1][2][3][4][5][6] Colorimetric sensing of a specific anion is a particularly attractive research topic because of its simplicity and naked eyes detectable nature, which allows visual detection of anions without resort to expensive spectroscopic instrumentation. 1,2,[7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Dicarboxylates are among the most attractive targets for anion recognition and sensing due to their critical roles in numerous metabolic processes such as the generation of highenergy phosphate bonds and the biosynthesis of important intermediates. 22,23 Detection of oxalate is particularly useful in food chemistry and in clinical analysis.…”

Section: Introductionmentioning

confidence: 99%

A New Chemosensing Ensemble for Colorimetric Detection of Oxalate in Water

Tang¹,

Liu²

2010

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

To realize highly selective recognition of oxalate in water, a new chemosensing ensemble that behaves highly selective colorimetric recognition of oxalate in water at pH 7.4 has been developed. The ensemble was constructed by a pyrrole containing mononuclear copper complex and chromeazurol S. The ensemble shows a highly selective recognition of oxalate through an obvious color change from blue to yellow upon the addition of oxalate, whereas, other dicarboxylates such as malonate, succinate, fumarate, maleate, glutarate, adipate, phthalate, isophthalate and terephthalate do not induce any noticeable color changes. The oxalate recognition process is not significantly affected by other coexisting dicarboxylate.

show abstract

Section: Introductionmentioning

confidence: 99%

A New Chemosensing Ensemble for Colorimetric Detection of Oxalate in Water

Tang¹,

Liu²

2010

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

show abstract

“…An approach for the construction of the core structure 1 and various derivatives, 2–13 among them (Fig. A), from the ring cleavage of suitably substituted xanthones (Scheme ), has been recently reported …”

Section: Resultsmentioning

confidence: 99%

“…Hydroxybenzophenones are not readily accessible and while numerous methods for their preparation have been described more are constantly in demand. It is known that the reactivity and biological activity of hydroxybenzophenones is linked to their acid‐base and metal chelating properties .…”

Section: Introductionmentioning

confidence: 99%

2, 2′‐Dihydroxybenzophenones and Derivatives. Efficient Synthesis and Structure Endoscopy by DFT and NMR. Credentials as Potent Antiinflammatory Agents.

et al. 2016

View full text Add to dashboard Cite

2,2’‐dihydroxybenzophenones and derivatives have been synthesized directly or by oxidation of their incipiently obtained benzylic alcohols by diverse efficient methods. Oxime and N‐acyl hydrazone derivatives have also been prepared. Their structure profile has been scrutinized by DFT/B3LYP‐6‐311++G** methodology, NMR spectroscopy and dihedral angle grid scan analysis. Energetically favorable conformations pointed to (i) an almost coplanar bifurcated 6‐membered H bridge in ketones, (ii) a single 6‐membered H bridge, accompanied by a 7‐membered H bonding interaction in oximes and (iii) a single 6‐membered H‐bridge in hydrazones. In the latter case, a stable conformation with an additional 9‐membered pseudo ring was also found. Highly deshielded protons in the NMR spectra are in accordance with the theoretically obtained findings on the H‐bonded conformers. Significant anti‐inflammatory activity of the compounds has been found by in vivo tests with their oxime and hydrazone derivatives showing the highest activity, hydrazone 11, in partucular, competing with marketed drugs. In silico docking studies point to the perspective potency of these structures as COX‐1/COX‐2 inhibitors.

show abstract

“…Im Unterschied zu diesem enantioselektiven Modus wäre eine gleichzeitige kolorimetrische oder UV‐Änderung unabhängig vom Enantiomerenverhältnis der Probe und daher geeignet für die Quantifizierung der Cysteingesamtmenge. Die optische Chemosensorik der absoluten Konfiguration von chiralen Verbindungen durch kovalente Substratmodifikation mit sorgfältig ausgewählten CD‐Sonden wurde von Berova, Rosini, Gawronski, Toniolo, Hosoi, Canary sowie Kim und Chin eingeführt. Vor kurzem wurde dieses Konzept – besonders mit der Einführung von irreversiblen Indikatorsubstitutionsexperimenten für quantitative ee ‐Bestimmungen – von Anslyn, Pu und anderen wiederentdeckt .…”

Section: Figureunclassified

Substratspezifische Analyse von Aminosäuren mit Sensoren für d/ l‐Cystein: umfassende stereochemische Untersuchungen in wässriger Lösung

Thanzeel

Wolf

2017

Angewandte Chemie

View full text Add to dashboard Cite

Das Auftreten von d‐Aminosäuren in Säugern und im Menschen ist von großer Bedeutung für die Lebenswissenschaften. d/l‐Aminosäuremischungen spielen eine Schlüsselrolle bei der menschlichen Physiologie und Pathologie; daher ist die Einführung künstlicher Rezeptoren für die Echtzeitquantifizierung der Konzentration und des d/l‐Verhältnisses von Aminosäuren vielversprechend für das Studium biologischer Prozesse und die Diagnose sowie Behandlung von Krankheiten. Die hier vorgestellte Detektionsmethode ist kompatibel mit wässrigen Lösungen und ermöglicht die rasche Bestimmung der absoluten Konfiguration, des ee‐Werts und der Gesamtmenge von Cystein bei mikromolaren Konzentrationen. Die Methode beruht auf schnellen UV‐ und CD‐Messungen, die akkurate stereochemische Informationen mit Proben über einen weiten Konzentrationsbereich und mit stark unterschiedlichen d/l‐Cysteinverhältnissen in simulierten Körperflüssigkeiten liefern. Konkurrenzexperimente zeigen, dass andere Aminosäuren und Biothiole die gezielte Cysteinanalyse nicht stören.

show abstract

Highly Stereospecific Generation of Helical Chirality by Imprinting with Amino Acids: A Universal Sensor for Amino Acid Enantiopurity

Cited by 98 publications

References 34 publications

A New Chemosensing Ensemble for Colorimetric Detection of Oxalate in Water

A New Chemosensing Ensemble for Colorimetric Detection of Oxalate in Water

2, 2′‐Dihydroxybenzophenones and Derivatives. Efficient Synthesis and Structure Endoscopy by DFT and NMR. Credentials as Potent Antiinflammatory Agents.

Substratspezifische Analyse von Aminosäuren mit Sensoren für d/ l‐Cystein: umfassende stereochemische Untersuchungen in wässriger Lösung

Contact Info

Product

Resources

About