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Structure Elucidation of Drug Resources Based on Inexperienced NMR Properties

基于原始核磁共振性质的药物资源结构解析

基本信息

批准号：
14207096
负责人：
KUSUMI Takenori
金额：
$ 23.71万
依托单位：
The University of Tokushima
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (A)
财政年份：
2002
资助国家：
日本
起止时间：
2002 至 2005
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-14207096/
关键词：
NMR Spectra Nuclear Magnetic Resonance Absolute Configuration NMR Phenomena NMR Solvent Effects Allenes Phosphorus C-P Couplings chirality modified Mosher's method NMR stereochemistry absolute configuration chiral anisotropic rea

项目摘要

1.A New NMR method to elucidate the absolute configuration of chiral allenes, which frequently occur in marine natural products and synthetic drugs was developed. This method utilizes 1,3-dipolar addition of a chiral nitrons, MPPO, to an allene possessing either an electron-withdrawing or donating substituent(s). By analyzing the stereochemistry of the adduct by NMR spectra, the chirality of the original allene is easily deduced.2.Phosphorus is an important element for organisms. It is included in compounds such as ATP and DNA, which are essential for life. Many works on the NMR properties of such the P-containing compounds, although there have been few study to use phosphorus as a key for elucidating the chemical structures of organic compounds. In the present study, C-P couplings are systematically investigated, by synthesizing various types of phosphates, aiming for development of new NMR method for structure elucidation.3.The modified Mosher's method, developed by our group, is an indispensable tool for determining the absolute configuration of organic compounds. It has been long believed that CDCl_3 must be used as an NMR solvent to obtain valid results. We reexamined the modified Mosher's method using several deutero-solvents such as C_6D_6,CD_3OD, and C_5D_5N, and concluded that the results obtained by the NMR spectra taken in these solvents are always correct.

1.建立了一种新的核磁共振方法，用于解析海洋天然产物和合成药物中常见的手性联烯的绝对构型。该方法利用手性硝子MPPO与具有吸电子或供电子取代基的丙二烯的1，3-偶极加成。通过核磁共振谱对加成物的立体化学进行分析，推测了原联烯的手性。2.磷是生物体的重要元素。它包含在ATP和DNA等化合物中，这些化合物对生命至关重要。尽管很少有研究将磷用作阐明有机化合物化学结构的关键，但许多工作都是关于这类含磷化合物的NMR性质。本研究通过合成不同类型的磷酸酯，系统地研究了C-P偶合反应，旨在发展新的NMR结构解析方法。3.本课题组发展的改进的Mosher方法是确定有机化合物绝对构型不可缺少的工具。长期以来，人们一直认为必须使用CDCl_3作为NMR溶剂才能获得有效的结果。我们用C_6D_6、CD_3OD和C_5D_5N等几种氘代溶剂重新检验了改进的Mosher法，并得出结论：在这些溶剂中用NMR谱所得到的结果总是正确的。