A primary hydrogen-deuterium isotope effect observed at the single-molecule level

Siran Lu*, Wen Wu Li, Dvir Rotem, Ellina Mikhailova, Hagan Bayley

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

The covalent chemistry of reactants tethered within a single protein pore can be monitored by observing the time-dependence of ionic current flow through the pore, which responds to bond making and breaking in individual reactant molecules. Here we use this 'nanoreactor' approach to examine the reaction of a quinone with a thiol to form a substituted hydroquinone by reductive 1,4-Michael addition. Remarkably, a primary hydrogen-deuterium isotope effect is readily detected at the single-molecule level during prototropic rearrangement of an initial adduct. The observation of individual reaction intermediates allows the measurement of an isotope effect whether or not the step involved is rate limiting, which would not be the case in an ensemble measurement.

Original languageAmerican English
Pages (from-to)921-928
Number of pages8
JournalNature Chemistry
Volume2
Issue number11
DOIs
StatePublished - Nov 2010
Externally publishedYes

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