Intramolecular proton transfer quenching in tryptophan and tryptamine: temperature dependence

Maurice R. Eftink; Dana Hu

doi:10.1117/12.182747

17 August 1994 Intramolecular proton transfer quenching in tryptophan and tryptamine: temperature dependence

Maurice R. Eftink, Dana Hu

Proceedings Volume 2137, Time-Resolved Laser Spectroscopy in Biochemistry IV; (1994) https://doi.org/10.1117/12.182747
Event: OE/LASE '94, 1994, Los Angeles, CA, United States

Abstract

There are two dominant intramolecular quenching reactions for the deactivation of the excited singlet state of tryptophan and its related chromophores. These mechanisms are charge transfer to an electrophilic side chain group and proton transfer from a side chain to the indole ring. When occurring in D₂O, the photoinduced proton transfer reaction results in an exchange of the hydrogen isotope at position 4 of the benzenoid ring of indole, which can be quantitated by ¹H-NMR studies. We have determined the rate constant for this photoinduced H-D exchange for tryptophan and some of its analogs as a function of temperature. We show that the proton transfer quenching reaction makes a large contribution to the quenching of tryptophan, whereas for other chromophores, charge transfer quenching must dominate.

Citation Download Citation

Maurice R. Eftink and Dana Hu "Intramolecular proton transfer quenching in tryptophan and tryptamine: temperature dependence", Proc. SPIE 2137, Time-Resolved Laser Spectroscopy in Biochemistry IV, (17 August 1994); https://doi.org/10.1117/12.182747

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