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.

为了阐明生化反应的机理，有必要研究相应生物活性化合物的立体化学，包括绝对构型。作为最近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：CHIRAL WORLD”。该数据库包含 1) 旋光度、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) 使用手性核磁共振进行手性识别具有强NMR各向异性效应的助剂，4）使用手性助剂的HPLC对映体拆分等。数据库通过互联网向全世界的研究人员开放。1．我们首先构建了手性数据库CHIRAL WORLD，其中包含旋光手性数据。、CD和UV光谱、绝对构型。2．打开数据库最理想的方式是网络系统，并且已经购买了数据库的计算机系统。3．我们开发了“手性邻苯二甲酸法”，可用于醇的对映体拆分和通过 X 射线晶体学测定绝对构型，这样的 HPLC 分辨率和 X 射线数据已注册。 .4. 我们开发了新的手性助剂2-甲氧基-2-(1-萘基)丙酸(MαNP酸)，它对于对映体拆分非常有效通过 HPLC 分离 MαNP 酯，MαNP 酸的萘基会产生非常强的 NMR 各向异性效应，因此可以通过 NMR 光谱法确定醇的绝对构型。这些手性数据也已纳入该数据库。