Monday, July 2, 2012

Design, Synthesis, and Photochemical Validation of Peptide Linchpins Containing the S,S-Tetrazine Phototrigger

Org. Lett.

http://pubs.acs.org/doi/abs/10.1021/ol301490h


The design, solid-phase synthesis, and photochemical validation of diverse peptide linchpins, containing the S,S-tetrazine phototrigger, have been achieved. Steady state irradiation or femtosecond laser pulses confirm their rapid photofragmentation. Attachment of peptides to the C- and N-termini will provide access to diverse constrained peptide constructs that hold the promise of providing information about early peptide/protein conformational dynamics upon photochemical release.

The S,S-tetrazine scaffold possesses a number of advantages when compared to other nonreversible trigger systems: (1) flash photolysis can be conducted with near-UV (λ=355 or 410 nm) laser pulses, which would not lead to damage of the peptide; (2) acceptable photolysis yields are observed; and (3) the thiocyanate photoproducts are relatively inert and provide a potentially useful IR probe.
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