Organic synthesis and Production based on Bioresources and Biocatalysis

基于生物资源和生物催化的有机合成与生产

• 批准号: 12660102
• 负责人: SUGAI Takeshi
• 金额: $ 2.3万
• 依托单位: Keio University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2000
• 资助国家: 日本
• 起止时间: 2000 至 2001
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-12660102/
• 关键词: Biocatalysts; kinetic resolution; hydrolysis; reduction; functional group transformation; glycoconjugates; 光学活性カルボン酸; リパーゼ; 速度論的光学分割; ニトリルヒドラターゼ; エステラーゼ; シアノヒドリン; アミノ糖; N-アセチルグルコサミン; Rhodococcus rhodochrous; パパイン

A variety of methods and theory controlling the reaction species and conditions in organic chemistry has recently been developed. Enzymes are exception. Chemists look upon enzymes as elegant reagents in molecular transformation, and many efforts have been devoted on the utilization of enzymes and microorganisms in synthetic organic chemistry. Needless to say, a remarkable advantage is that enzymes are the catalysts whose supply from microorganisms, animals, and plants never quit, as the resources can be reproduced in a self-production manner. In this study supported by the grant-in-aid (2000-2001), moreover, the starting materials were secured from the new source, bio-mass and fermentation products.The achievements were; 1) Synthesis of enantioemrically enriched compounds by anti-Prelog yeast (Yamadazyma farinosa)-catalyzed asymmetric reduction; 2) Asymmetrization and kinetic resolution by means of a yeast (Torulaspora delbrueckii) catalyzed reduction; 3) Clarification of some phenomena observed in lipase-catalyzed hydrolysis and esterification toward the establishment of efficient kinetic resolution; 4) application on the synthesis of glycoconjugates: N-acetylglucosaminyl-Cbz-asparagine; 5) Integrated combined process of chemo-enzymatic procedure: synthesis of (R)-2-naphthylmethoxyacetic acid.

近年来发展了许多控制有机化学反应物种和条件的方法和理论。酶是个例外。化学家们把酶看作是分子转化中的优良试剂，许多人致力于酶和微生物在有机合成化学中的应用。不用说，酶的一个显著优点是，酶是催化剂，微生物、动物和植物的供应永不停止，因为这些资源可以以自我生产的方式再生。在这项研究中，本论文的主要研究成果有：1）利用反Prelog酵母合成对映体富集化合物（Yamadazyma farinosa）催化的不对称还原; 2）酵母的不对称化和动力学拆分（Torulasporadelbrueckii）催化还原; 3）澄清在脂肪酶催化水解和酯化中观察到的一些现象，以建立有效的动力学拆分; 4）在糖缀合物合成中的应用：N-乙酰葡糖胺-Cbz-天冬酰胺; 5）化学-酶法的集成组合过程：（R）-2-萘甲氧基乙酸合成

项目成果

M.Suzuki, C.Nagasawa, T.Sugai: "Synthesis of Indanoxazolidinone based on the Lipase-catalyzed Resolution of the Corresponding N-Carbamylamino Derivative"Tetrahedron. 57. 4841-4848 (2001)

M.Suzuki、C.Nagasawa、T.Sugai：“基于相应 N-氨基甲酰胺衍生物的脂肪酶催化拆分的茚满恶唑烷酮的合成”四面体。

T. Yamazaki, A. Kuboki, H. Ohta, T. Mitzel. L.A. Paquette, T. Sugai: "Yamadazyma farinosa IFO 10896-Mediated Reduction of 4,4-Dimethoxy-2-butanone as The Key-Step for the Preparatation of 1,3-Diols With Unsymmetrical Substituents"Synth. Commun.. 30. 3061-

T.山崎，A.久保木，H.太田，T.米泽尔。

M.Suzuki, C.Nagasawa, T.Sugai: "Synthesis of Indanoxazolidinone based on the Lipase-catalyzed Resolution of the cornesponding N-carbonylamino Derivative"Tetrahedron. 57. 4841-4848 (2001)

M.Suzuki、C.Nagasawa、T.Sugai：“基于相应 N-羰氨基衍生物的脂肪酶催化拆分的茚满恶唑烷酮的合成”四面体。

Y.Tokuda, Y.Takahashi, K.Matoishi, Y.Ito, T.Sugai: "Expedttious Route to GlcNAc-Cbz-Asn by chemo-enzymatic Synthesis"Synlett. 57-60 (2002)

Y.Tokuda、Y.Takahashi、K.Matoishi、Y.Ito、T.Sugai：“通过化学酶合成快速合成 GlcNAc-Cbz-Asn 的途径”Synlett。

T.Sugai, T.Kajimoto: ""Synthesis of Biologically Relevant Monosaccharides", in "Glycoscience-Chenstry and Chemical Biology""Springer-Verlag-GmbH. 907-1021 (2001)

T.Sugai、T.Kajimoto：“生物相关单糖的合成”，载于“糖科学-化学和化学生物学”“Springer-Verlag-GmbH”。