Stereoselective Phosphorylation of Diols and Carbohydrates with N-Phosphoryl Oxazolidinones: Application to the Rapid Synthesis of Phosphoglycerides

N-磷酰恶唑烷酮对二醇和碳水化合物进行立体选择性磷酸化：在磷酸甘油酯快速合成中的应用

• 批准号: EP/D00747X/1
• 负责人: Simon Jones
• 金额: $ 23.99万
• 依托单位: University of Sheffield
• 依托单位国家: 英国
• 项目类别: Research Grant
• 财政年份: 2006
• 资助国家: 英国
• 起止时间: 2006 至 无数据
• 项目状态: 已结题
• 来源: https://gtr.ukri.org/projects?ref=EP%2FD00747X%2F1
• 关键词: Stereoselective; Phosphorylation; Diols; Carbohydrates; Phosphoryl

Many substances in Nature exist as two different forms called enantiomers. These molecules have the same number of atoms and are connected in the same way, except the arrangement of some of the atoms is different. Your hands are both enantiomers - both are made up of the same bits (a palm, one thumb and four different fingers) and all are connected in the same way (thumb, first finger, second finger and so on). However the order of connectivity is different which leads to your left and right hand being related as non-superimposable mirror images. Objects or substances that are non-superimposable mirror images are called chiral. Each of these chiral substances in Nature and many pharmaceutical ingredients have different biological activities and so much effort is devoted to developing chemical reactions that can selectively produce only one of these forms. Research from these laboratories has developed a completely new method for achieving such a transformation by formation of a phosphate ester. Such a reaction is incredibly useful since the products formed from this reaction can be used as chemical building blocks to construct other larger materials. The purpose of this project is to build upon this new methodology and to attempt to make phosphate esters of more complex molecules such as carbohydrates, glycerides and inositols. The phosphate ester products of these reactions are extremely important and valuable materials for use in biology where they can be used as molecular tools to investigate how cells work. The added advantage of our methodology is that it can be carried out selectivity, quickly and in one reaction vessel, significantly simplifying the time and effort required to prepare these substances.We will demonstrate the effectiveness of this work by constructing several biologically active target molecules that will be of use to collaborators in the Department of Genomic Medicine here at the University of Sheffield.We will investigate ways to develop a catalyst for this reaction system that will further simplify the procedure and reduce the cost of production of these highly desirable products even further.

自然界中的许多物质以两种不同的形式存在，称为对映体。这些分子具有相同数量的原子，并且以相同的方式连接，除了一些原子的排列不同。你的手都是对映异构体-都是由相同的部分（一个手掌，一个拇指和四个不同的手指）组成的，并且都以相同的方式连接（拇指，第一个手指，第二个手指等）。然而，连接的顺序是不同的，这导致你的左手和右手作为不可重叠的镜像相关。不能重叠的镜像的物体或物质称为手性。自然界中的这些手性物质和许多药物成分中的每一种都具有不同的生物活性，并且如此多的努力致力于开发可以选择性地仅产生这些形式中的一种的化学反应。这些实验室的研究已经开发出一种全新的方法，通过形成磷酸酯来实现这种转化。这种反应非常有用，因为从这种反应形成的产物可以用作化学构建块来构建其他更大的材料。该项目的目的是建立在这种新方法的基础上，并试图制造更复杂分子的磷酸酯，如碳水化合物，甘油酯和肌醇。这些反应的磷酸酯产物在生物学中是极其重要和有价值的材料，它们可以用作研究细胞如何工作的分子工具。我们的方法的附加优点是它可以选择性地、快速地和在一个反应容器中进行，我们将通过构建几种生物活性靶分子来证明这项工作的有效性，这些靶分子将对谢菲尔德大学基因组医学系的合作者有用。我们将研究开发用于该反应体系的催化剂，其将进一步简化该过程并甚至进一步降低这些高度期望的产物的生产成本。