An algorithm for the deconvolution of mass spectrosopic patterns in isotope labeling studies. Evaluation for the hydrogen-deuterium exchange reaction in ketones

Christian C. Gruber, Gustav Oberdorfer, Constance V. Voss, Jennifer M. Kremsner, C. Oliver Kappe, Wolfgang Kroutil

Research output: Contribution to journalArticleResearchpeer-review

Abstract

(Graph Presented) An easy to use computerized algorithm for the determination of the amount of each labeled species differing in the number of incorporated isotope labels based on mass spectroscopic data is described and evaluated. Employing this algorithm, the microwave-assisted synthesis of various α-labeled deuterium ketones via hydrogen-deuterium exchange with deuterium oxide was optimized with respect to time, temperature, and degree of labeling. For thermally stable ketones the exchange of α-protons was achieved at 180°C within 40-200 min. Compared to reflux conditions, the microwave-assisted protocol led to a reduction of the required reaction time from 75-94 h to 40-200 min. The α-labeled deuterium ketones were reduced by biocatalytic hydrogen transfer to the corresponding enantiopure chiral alcohols and the deconvolution algorithm validated by regression analysis of a mixture of labeled and unlabeled ketones/alcohols.

Original languageEnglish
Pages (from-to)5778-5783
Number of pages6
JournalJournal of Organic Chemistry
Volume72
Issue number15
DOIs
Publication statusPublished - 20 Jul 2007

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Deuterium
Deconvolution
Ketones
Isotopes
Labeling
Hydrogen
Microwaves
Alcohols
Deuterium Oxide
Regression analysis
Protons
Labels
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

An algorithm for the deconvolution of mass spectrosopic patterns in isotope labeling studies. Evaluation for the hydrogen-deuterium exchange reaction in ketones. / Gruber, Christian C.; Oberdorfer, Gustav; Voss, Constance V.; Kremsner, Jennifer M.; Kappe, C. Oliver; Kroutil, Wolfgang.

In: Journal of Organic Chemistry, Vol. 72, No. 15, 20.07.2007, p. 5778-5783.

Research output: Contribution to journalArticleResearchpeer-review

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AB - (Graph Presented) An easy to use computerized algorithm for the determination of the amount of each labeled species differing in the number of incorporated isotope labels based on mass spectroscopic data is described and evaluated. Employing this algorithm, the microwave-assisted synthesis of various α-labeled deuterium ketones via hydrogen-deuterium exchange with deuterium oxide was optimized with respect to time, temperature, and degree of labeling. For thermally stable ketones the exchange of α-protons was achieved at 180°C within 40-200 min. Compared to reflux conditions, the microwave-assisted protocol led to a reduction of the required reaction time from 75-94 h to 40-200 min. The α-labeled deuterium ketones were reduced by biocatalytic hydrogen transfer to the corresponding enantiopure chiral alcohols and the deconvolution algorithm validated by regression analysis of a mixture of labeled and unlabeled ketones/alcohols.

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