Ludvíková Lucie, Štacko Peter, Sperry Jonathan, Klán Petr
Department of Chemistry and RECETOX, Faculty of Science , Masaryk University , Kamenice 5 , 625 00 Brno , Czech Republic.
School of Chemical Sciences , University of Auckland , 23 Symonds Street , Auckland , New Zealand.
J Org Chem. 2018 Sep 21;83(18):10835-10844. doi: 10.1021/acs.joc.8b01545. Epub 2018 Aug 7.
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.
通过稳态吸收和发射光谱、纳秒瞬态吸收光谱以及化学分析，研究了孟加拉玫瑰红在磷酸盐缓冲盐水中对色氨酸和酪氨酸的N - 乙酰衍生物的光敏交联作用。在缺氧条件下，以孟加拉玫瑰红作为牺牲性氧化剂，这些氨基酸会发生交联形成二聚体和更高的寡聚产物，而在曝气溶液中，它们主要与孟加拉玫瑰红产生的单线态氧反应。这项研究全面地揭示了孟加拉玫瑰红对这两种氨基酸进行光敏交联的第一步。研究结果有助于孟加拉玫瑰红及相关染料未来的应用，如光化学组织黏合或可见光光催化。
