A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay

Stephanie A. Valenzuela; Hannah S.N. Crory; Chao Yi Yao; James R. Howard; Gabriel Saucedo; A. Prasanna de Silva; Eric V. Anslyn

doi:10.1002/ange.202101004

A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay

Stephanie A. Valenzuela, Hannah S.N. Crory, Chao Yi Yao, James R. Howard, Gabriel Saucedo, A. Prasanna de Silva, Eric V. Anslyn^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

196 Downloads (Pure)

Abstract

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. 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 E₂ and Wittig reactions gave errors of ±3 %. Furthermore, we developed variants of the IDA for which the color may be tuned to optimize the response for the human eye.

Original language	English
Pages (from-to)	13819-13823
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	25
Early online date	15 Mar 2021
DOIs	https://doi.org/10.1002/ange.202101004 https://doi.org/10.1002/anie.202101004
Publication status	Published - 14 Jun 2021

Bibliographical note

Publisher Copyright:
© 2021 Wiley-VCH GmbH

Keywords

alkene stereochemistry
colorimetric assays
dihydroxylation
high-throughput screening
host–guest systems

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/ange.202101004Licence: Unspecified
10.1002/anie.202101004Licence: Unspecified

A Colorimetric Method for Quantifying Cis‐ and Trans‐Alkenes Using an Indicator Displacement Assay
Copyright 2021 Wiley. This work is made available online in accordance with the publisher’s policies. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 1.49 MBLicence: Unspecified

Shape-switching studies with cyclophanes and indicator displacement assays with boronic acids
Crory, H. (Author), De Silva, A. (Supervisor) & Anslyn, E. (Supervisor), Jul 2021
Student thesis: Doctoral Thesis › Doctor of Philosophy

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title = "A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay",

abstract = "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. 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 E2 and Wittig reactions gave errors of ±3 %. Furthermore, we developed variants of the IDA for which the color may be tuned to optimize the response for the human eye.",

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author = "Valenzuela, {Stephanie A.} and Crory, {Hannah S.N.} and Yao, {Chao Yi} and Howard, {James R.} and Gabriel Saucedo and {de Silva}, {A. Prasanna} and Anslyn, {Eric V.}",

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doi = "10.1002/ange.202101004",

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T1 - A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay

AU - Valenzuela, Stephanie A.

AU - Crory, Hannah S.N.

AU - Yao, Chao Yi

AU - Howard, James R.

AU - Saucedo, Gabriel

AU - de Silva, A. Prasanna

AU - Anslyn, Eric V.

PY - 2021/6/14

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N2 - 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. 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 E2 and Wittig reactions gave errors of ±3 %. Furthermore, we developed variants of the IDA for which the color may be tuned to optimize the response for the human eye.

AB - 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. 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 E2 and Wittig reactions gave errors of ±3 %. Furthermore, we developed variants of the IDA for which the color may be tuned to optimize the response for the human eye.

KW - alkene stereochemistry

KW - colorimetric assays

KW - dihydroxylation

KW - high-throughput screening

KW - host–guest systems

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JO - Angewandte Chemie - International Edition

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IS - 25

ER -

A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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Student theses

Shape-switching studies with cyclophanes and indicator displacement assays with boronic acids

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