This poster describes the kinetics of thiol�thioester exchange and the development of a reversible binding system based on the reaction.  Thioesters are thermodynamically-activated equivalents of carboxylic acids that have been implicated as potentially important to the origin of life on Earth.  We studied the kinetics of thiol�thioester exchange to measure the rate of the reaction in water versus the destructive reaction of thioester hydrolysis.  Our study confirmed that the exchange reaction can compete effectively with hydrolysis at mild pH.  We pursued this line of investigation to develop a biologically-compatible system for binding molecules to surfaces reversibly, in water, at room temperature, near neutral pH, without the use of harsh reagents.  Collectively, the projects described here can be viewed as a model for how basic research on chemistry pertinent to the origin of life can yield knowledge relevant to the development of technology with clear practical value.

Thiol–thioester exchange: Reaction kinetics, practical applications, and implications for the origin of life

242nd National Meeting (2011)

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