Probing the Basis of Donor/Acceptor MATCH

该项目的重点是发展碳水化合物化学中供体和受体反应物之间匹配的基本理解，从30年前的经验观察中建立，一些供体糖苷化给定的受体-OH比其他人更好。正戊烯基原酸酯（NPOE）作为糖基供体显示出极好的区域选择性，超过了正戊烯基糖苷。通过对这些供体的早期阳离子中间体的分析，将推断出这种选择性增强的起源。有了这个奖项，有机和大分子化学计划正在支持Bert O.天然产品和糖技术研究所的弗雷泽-里德说。Fraser-Reid博士正在开发可预测的、可控的多糖合成方法。这些复杂的分子，在各种各样的生物和生物化学过程中发挥核心作用，包括细胞信号传导和细胞-细胞识别，是众所周知的难以合成制备。通过专注于了解影响碳水化合物反应性的因素，Fraser-Reid博士正在开发新的有效合成方法，使这些重要分子更容易进行研究和最终开发，例如，疫苗或诊断工具。

This project focuses on development of a fundamental understanding of the match between donor and acceptor reactants in carbohydrate chemistry, building from an empirical observation 30 years ago that some donors glycosidate a given acceptor-OH better than others. n-Pentenyl orthoesters (NPOEs) display exquisite regioselectivity as glycosyl donors, exceeding that of n-pentenyl glycosides. Through analysis of the early cationic intermediates of these donors, the origin of this selectivity enhancement will be deduced.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Bert O. Fraser-Reid, of the Natural Products and Glycotechnology Research Institute. Dr. Fraser-Reid is developing methods for the predictable, controlled synthesis of polysaccharides. These complex molecules, playing central roles in a wide variety of biological and biochemical processes, including cellular signaling and cell-cell recognition, are notoriously difficult to prepare synthetically. By focusing on an understanding of the factors influencing the reactivity of carbohydrates, Dr. Fraser-Reid is developing new and efficient synthetic methods, making these important molecules more accessible for study and ultimate development as, e.g., vaccines or diagnostic tools.