Probing the Basis of Donor/Acceptor MATCH

本项目的重点是发展对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，这是基于30年前的一项经验观察，即一些供体比其他供体更能使给定的受体- oh糖苷化。正戊基正酯（npoe）作为糖基供体表现出良好的区域选择性，优于正戊基糖苷。通过对这些供体的早期阳离子中间体的分析，推导出选择性增强的原因。有了这个奖项，有机和大分子化学项目支持了天然产物和糖苷技术研究所的Bert O. Fraser-Reid博士的研究。弗雷泽-里德博士正在开发可预测的、可控的多糖合成方法。这些复杂的分子在多种生物和生化过程中发挥着核心作用，包括细胞信号传导和细胞-细胞识别，众所周知，很难合成。通过专注于了解影响碳水化合物反应性的因素，Fraser-Reid博士正在开发新的高效合成方法，使这些重要分子更容易用于研究和最终开发，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.