ArticleEuropean journal of organic chemistry2021
A Kinetic Photometric Assay for the Quantification of the Open-Chain Content of Aldoses.
Article in European journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed, 6 citations in OpenAlex.
- The synthesis of higher-carbon sugar alcohols via indium-mediated acyloxyallylation as potential phase change materials.Monatshefte fur chemie · 2025Article
- A Kinetic Photometric Assay for the Quantification of the Open-Chain Content of Aldoses.European journal of organic chemistry · 2021Article
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6 authors at 2 institutions in 1 country.
Funding
Abstract
Aldoses exist predominantly in the cyclic hemiacetal form, which is in equilibrium with the open-chain aldehyde form. The small aldehyde content hampers reactivity when chemistry addresses the carbonyl moiety. This low concentration of the available aldehyde is generally difficult to ascertain. Herein, we demonstrate a new kinetic determination of the (minute) open-chain content (OCC) of aldoses. This kinetic approach exploits the aldehyde-selectivity of 2-aminobenzamidoxime (ABAO), which furnishes a strongly UV-active adduct. Simple formation curves can be measured in a photometer or plate reader for high-throughput screening. Under pseudo-first order kinetics, these curves correlate with a prediction model yielding the relative OCC. The OCCs of all parent aldoses (pentoses and hexoses) were determined referencing against the two tetroses with exceptionally high OCCs and were in very good agreement with literature data. Additionally, the assay was extended towards higher-carbon sugars with unknown OCC and also applied to rationalise a lack of reactivity observed in a recent synthetic investigation.
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