A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay
| Autor: | Gabriel Saucedo, James R. Howard, Chao-Yi Yao, A. Prasanna de Silva, Stephanie A. Valenzuela, Hannah S. N. Crory, Eric V. Anslyn |
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| Přispěvatelé: | De Silva, Amilra |
| Rok vydání: | 2021 |
| Předmět: |
Molecular Structure
010405 organic chemistry Chemistry Stereochemistry Diastereomer Stereoisomerism General Chemistry General Medicine Alkenes 010402 general chemistry 01 natural sciences Catalysis Article 0104 chemical sciences chemistry.chemical_compound Dihydroxylation Wittig reaction Colorimetry Indicator displacement assay Cis–trans isomerism Boronic acid |
| Zdroj: | Crory, H, Yao, C, De Silva, A (ed.), Anslyn, E, Valenzuela, S, Howard, J & Saucedo, G 2021, ' A Colorimetric Method for Quantifying Cis- and Trans-Alkenes Using an Indicator Displacement Assay ', Angewandte Chemie, pp. 1-6 . https://doi.org/10.1002/ange.202101004 Angew Chem Int Ed Engl |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.202101004 |
| Popis: | A colorimetric indicator displacement assay (IDA) amenable to high-throughput experimentation was developed to determine the percentage of cis- and trans-alkenes. Using 96-well plates two steps are performed: a reaction plate for dihydroxylation of the alkenes followed by an IDA screening plate consisting of an indicator and a boronic acid. The dihydroxylation generates either erythro or threo vicinal diols from cis- or trans-alkenes depending upon their syn- or anti-addition mechanisms. Threo diols preferentially associate with the boronic acid due to the creation of more stable boronate esters, thus displacing the indicator to a greater extent. The generality of the protocol was demonstrated using seven sets of cis- and trans-alkenes. Further, blind mixtures of cis- and trans-alkenes were made resulting in an average error of ±2% in the percentage of cis- or trans-alkenes, and implementing E(2) and Wittig reactions gave errors of ±3%. Furthermore, we developed variants of the IDA that alter the color changes to optimize the response to the human eye. |
| Databáze: | OpenAIRE |
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