Choose your leaving group: selective photodeprotection in a mixture of p HP-caged compounds by VIPER excitation.

Autor:	van Wilderen LJGW; Johann Wolfgang Goethe-University, Institute of Biophysics Max-von-Laue-Str. 1 60438 Frankfurt am Main Germany bredenbeck@biophysik.uni-frankfurt.de., Kern-Michler D; Johann Wolfgang Goethe-University, Institute of Biophysics Max-von-Laue-Str. 1 60438 Frankfurt am Main Germany bredenbeck@biophysik.uni-frankfurt.de., Neumann C; Johann Wolfgang Goethe-University, Institute of Biophysics Max-von-Laue-Str. 1 60438 Frankfurt am Main Germany bredenbeck@biophysik.uni-frankfurt.de., Reinfelds M; Johann Wolfgang Goethe-University, Institute of Organic Chemistry and Chemical Biology Max-von-Laue-Str. 7 60438 Frankfurt am Main Germany., von Cosel J; Johann Wolfgang Goethe-University, Institute of Physical and Theoretical Chemistry Max-von-Laue-Str. 7 60438 Frankfurt am Main Germany., Horz M; Johann Wolfgang Goethe-University, Institute of Physical and Theoretical Chemistry Max-von-Laue-Str. 7 60438 Frankfurt am Main Germany., Burghardt I; Johann Wolfgang Goethe-University, Institute of Physical and Theoretical Chemistry Max-von-Laue-Str. 7 60438 Frankfurt am Main Germany., Heckel A; Johann Wolfgang Goethe-University, Institute of Organic Chemistry and Chemical Biology Max-von-Laue-Str. 7 60438 Frankfurt am Main Germany., Bredenbeck J; Johann Wolfgang Goethe-University, Institute of Biophysics Max-von-Laue-Str. 1 60438 Frankfurt am Main Germany bredenbeck@biophysik.uni-frankfurt.de.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2023 Feb 08; Vol. 14 (10), pp. 2624-2630. Date of Electronic Publication: 2023 Feb 08 (Print Publication: 2023).
DOI:	10.1039/d2sc06259c
Abstrakt:	Photocages are light-triggerable molecular moieties that can locally release a pre-determined leaving group (LG). Finding a suitable photocage for a particular application may be challenging, as the choice may be limited by for instance the optical or physicochemical properties of the system. Using more than one photocage to release different LGs in a reaction mixture may even be more difficult. In this work an experimental strategy is presented that allows us to hand-pick the release of different LGs, and to do so in any order. This is achieved by using isotopologue photocage-LG mixtures in combination with ultrafast VIbrationally Promoted Electronic Resonance (VIPER) excitation. The latter provides the required molecular selectivity simply by tuning the wavenumber of the used IR pulses to the resonance of a specific photocage isotopologue, as is demonstrated here for the para -hydroxyphenacyl ( p HP) photocage. For spectroscopic convenience, we use isotopologues of the infrared (IR) spectroscopic marker -SCN as different LGs. Especially for applications where fast LG release is required, p HP is found to be an excellent candidate, as free LG formation is observed to occur with a 10 ps lifetime. The devised strategy may open up new complex uncaging applications, where multiple LGs can be formed locally on a short time scale and in any sequence. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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