Photosensitized Cross-Linking of Tryptophan and Tyrosine Derivatives by Rose Bengal in Aqueous Solutions
| Authors | |
|---|---|
| Year of publication | 2018 |
| Type | Article in Periodical |
| Magazine / Source | Journal of Organic Chemistry |
| MU Faculty or unit | |
| Citation | |
| Web | https://pubs.acs.org/doi/10.1021/acs.joc.8b01545 |
| Doi | http://dx.doi.org/10.1021/acs.joc.8b01545 |
| Keywords | LASER FLASH-PHOTOLYSIS; AROMATIC-AMINO-ACIDS; EXCITED-STATE CHEMISTRY; SINGLET OXYGEN; SENSITIZED PHOTOOXIDATION; MEMBRANE-PROTEINS; OXIDATION; PEPTIDES; RESIDUES; SKIN |
| Description | Photosensitized cross-linking of N-acetyl derivatives of tryptophan and tyrosine by rose bengal in phosphate buffer saline was studied by steady-state absorption and emission spectroscopy, nanosecond transient absorption spectroscopy, and chemical analyses. These amino acids undergo cross-linking to form dimeric and higher oligomeric products under anoxic conditions with rose bengal as a sacrificial oxidant, whereas they react predominantly with singlet oxygen produced by rose bengal in aerated solutions. This investigation provides a comprehensive view into the first steps of rose bengal photosensitized cross-linking of these two amino acids. The results can be helpful for future applications of rose bengal and related dyes, such as photochemical tissue bonding or visible light photocatalysis. |
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