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Research for the Development, Construction, and Management of the Chirality Database

手性数据库开发、建设与管理研究

基本信息

批准号：
10554035
负责人：
HARADA Nobuyuki
金额：
$ 8.9万
依托单位：
Tohoku University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (B)
财政年份：
1998
资助国家：
日本
起止时间：
1998 至 2001
项目状态：
已结题

项目摘要

To clarify the mechanism of biochemical reactions, it is essential to study the stereochemistry of corresponding bioactive compounds including absolute configurations. As the fundamental information of bioactive compounds and optically active organic materials recently developed, we are constructing the "Chirality Database: CHIRAL WORLD." The database contains 1) data of optical rotation, circular dichroism, and absolute stereochemistry, 2) X-ray crystallography and absolute configuration, 3) chiral recognition by NMR using chiral auxiliaries with strong NMR anisotropy effect, 4) enantioresolution of racemates by HPLC using chiral auxiliaries, etc. The database is opened for researchers worldwide via internet.1. We have first constructed the chirality database, CHIRAL WORLD, which contains chiral data of optical rotation, CD and UV spectra, and absolute configurations.2. To open the database, the internet system is the most ideal, and the computer system for the database has been purchased.3. The most powerful method for determining absolute configurations is X-ray crystallography. We have developed the "Chiral Phthalic Acid method" which is useful for both enantioresolution of alcohols and determination of absolute configuration by X-ray crystallography. Such HPLC resolution and X-ray data have been registered.4. We have developed the new chiral auxiliary, 2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid), which is very powerful for enantioresolution of aliphatic alcohols by HPLC separation of MαNP esters. The naphthyl group of MαNP acid induces very strong NMR anisotropy effect, by which the absolute configuration of alcohols could be determined by NMR spectroscopy. Those chirality data have also been incorporated into this database.

研究生物活性化合物的立体化学，包括其绝对构型，对于阐明生物化学反应的机理至关重要。作为近年来开发的生物活性化合物和光学活性有机材料的基础信息，我们正在构建“手性数据库：手性世界”。该数据库包含1）旋光、圆二色性和绝对立体化学数据，2）X射线晶体学和绝对构型，3）使用具有强NMR各向异性效应的手性助剂通过NMR进行手性识别，4）使用手性助剂通过HPLC进行外消旋体的对映体拆分等。该数据库通过互联网向全球研究人员开放。我们首先建立了手性数据库CHIRAL WORLD，其中包含旋光度、CD和UV光谱以及绝对构型的手性数据.数据库的开放以网络系统最为理想，数据库的计算机系统已经购置.确定绝对构型最有效的方法是X射线晶体学。我们发展了手性邻苯二甲酸法，该方法可用于醇类化合物的手性拆分和X射线晶体学测定绝对构型。这种HPLC分辨率和X射线数据已经注册。我们开发了一种新的手性助剂2-甲氧基-2-（1-萘基）丙酸（MαNP acid），它对脂肪醇的对映体拆分有很强的作用，并通过高效液相色谱法分离了MαNP酯。MαNP酸的萘基具有很强的NMR各向异性效应，利用该效应可以用NMR谱确定醇的绝对构型。这些手性数据也已纳入该数据库。