Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, Japan.
Chem Rec. 2023 Nov;23(11):e202300198. doi: 10.1002/tcr.202300198. Epub 2023 Sep 7.
Histidine photooxygenation has been the subject of extensive investigation for many years. The intricate nature of histidine distinguishes it from other amino acids, as its side chain readily undergoes changes in charge state and tautomerization in response to pH, and the polarity of the imidazole ring inverts upon oxidation. This complexity gives rise to a diverse range of oxidation products and mechanisms, posing challenges in their interpretation. This review aims to provide a thorough overview of the chemistry involved in histidine photooxygenation, encompassing a comprehensive analysis of resulting products, mechanisms engaged in their formation, and analytical techniques that have contributed to their identification. Additionally, it explores a wide range of applications stemming from this transformation, offering valuable insights into its practical implications in fields such as materials science, biomedical research, and drug development. By bridging the existing gap in literature, this review serves as a resource for understanding the intricacies of histidine photooxygenation and its diverse ramifications.
组氨酸光氧化作用多年来一直是广泛研究的课题。组氨酸的复杂性质使其有别于其他氨基酸，因为其侧链很容易在电荷状态和互变异构方面发生变化，并且咪唑环的极性在氧化时会反转。这种复杂性导致了广泛的氧化产物和机制，给它们的解释带来了挑战。本综述旨在全面概述组氨酸光氧化作用所涉及的化学，包括对所得产物、形成机制的综合分析，以及有助于其鉴定的分析技术。此外，还探讨了源自这种转化的广泛应用，为其在材料科学、生物医学研究和药物开发等领域的实际意义提供了有价值的见解。通过弥合文献中的现有差距，本综述为理解组氨酸光氧化作用及其广泛影响的复杂性提供了资源。
