RUI: Bioorganic Chemistry of Eumelanin

通过这项本科生研究奖(RUI)，化学系的生命过程化学项目资助来自奥伯林学院的Jason Belitsky博士研究真黑素的形成和结构，真黑素是一种在人体内用作光保护剂的色素。目前的研究表明，真黑素是由二羟基吲哚齐聚物和纳米颗粒自组装而成的。通过迭代Suzuki偶联路线将合成定义明确的二羟基吲哚低聚物，并将利用核磁共振、UV-Vis光谱和扫描电子显微镜(SEM)等技术研究这些低聚物及其氧化产物和金属离子的自组装。从定义明确的低聚物形成微米和纳米级组件的结构-活性关系将被寻求提供对真黑素结构的分子水平的理解。从长远来看，了解真黑素的化学和光物理性质是一个重要的目标，因为它的生物学功能和潜在的病理作用尚未完全确定。尽管公众对黑色素感兴趣，但其复杂性和异质性为其研究提供了障碍。黑色素当然是一种生物聚合物，在人类生物学中具有重要作用，在皮肤和头发的生物学中具有特别重要的意义，并可能与皮肤癌等病理疾病有关。更好地了解黑色素的化学将有助于阐明它们在人类生物学和疾病中的作用，以及在工程、环境和生物应用中基于黑色素的材料中的作用。然而，对黑色素的基本了解远远落后于其他生物聚合物，如蛋白质和DNA。在这里，Beltisky小组将使用合成模型化合物，采用“自下而上”的方法来理解真黑素的形成和结构。与别里茨基团队的情况一样，本科生研究人员将构成研究团队的中坚力量。此外，PI计划将这项研究与他在奥伯林学院的教学相结合，这样每年有多达60名本科生接触到研究水平的合成化学转化，作为他们二年级水平有机化学实验室课程经验的一部分。

With this Research at Undergraduate Institutions (RUI) award, the Chemistry of Life Processes Program in the Chemistry Division is funding Dr. Jason Belitsky from Oberlin College to study the formation and structure of eumelanin, a pigment in humans that serves as a photoprotective agent. Current research suggests that eumelanin is formed from the self-assembly of dihydroxyindole oligomers and nanoparticles. Well-defined dihydroxyindole oligomers will be synthesized via iterative Suzuki coupling routes, and the self-assembly of these oligomers, their oxidation products, and metal ions will be studied using techniques such as NMR, UV-Vis spectroscopy, and scanning electron microscopy (SEM). Structure-activity relationships in the formation of micro- and nano- scale assemblies from well-defined oligomers will be sought to provide a molecular level understanding of eumelanin structure. In the long term, understanding the chemical and photophysical properties of eumelanin is an important goal given its incompletely defined biological functions and potential role in pathologies. Despite public interest in melanin, its complexity and heterogeneity have provided obtacles to its study. Melanin is certainly a biopolymer with an important role in human biology, with particular significance in the biology of the skin and hair and a likely connection to pathologies such as skin cancer. A greater understanding of the chemistry of melanins would help illuminate their roles in human biology and disease, as well as in melanin-based materials for engineering, environmental, and biological applications. However, a fundamental understanding of melanins lags far behind other biopolymers, such as proteins and DNA. Here, the Beltisky group will use synthetic model compounds in a "bottom-up" approach toward the understanding of the formation and structure of eumelanin. As has been the case in the Belitsky group, undergraduate researchers will form the backbone of the research team. Additionally, the PI plans to integrate the research with his teaching at Oberlin College, such that up to 60 undergraduates per year get exposure to research-level synthetic chemistry transformations as part of their sophomore-level organic chemistry laboratory course experience.