Screening of New Biocatalysts and Its Application to the Synthesis of Biologically Active Compounds

新型生物催化剂的筛选及其在生物活性化合物合成中的应用

• 批准号: 09660120
• 负责人: SUGAI Takeshi
• 金额: $ 2.18万
• 依托单位: Depatment of Chemistry, 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: 1997
• 资助国家: 日本
• 起止时间: 1997 至 1998
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09660120/
• 关键词: Amino Alcohol; Ceramide; Lipase; Kinetic Resolution; Pheromone; Amino Sugar; Regioselective Acylation; フェリエ反応; グリカ-ル; 位置選択的保護; 〔3,3〕-シグマトロピー転位

Results of screeing of new biocatalysts and its application to the synthesis of biologically active compounds are summalized as follows. 1) pivotal role of (E)-3-carbamoyl-1-propenylboronic acid in the combination of Suzuki-Miyaura coupling and enzyme reactions : synthesis of (3E,5E)- and (3E,5Z)-6-phenyl-3,5-hexadienoic Acid ; 2) biocatalyst-mediated efficient preparation of highly enantiomerically enriched (R)-5-hexanolide ; 3) A chemo-enzymatic synthesis of D-allosamine derivatives from Tri-O-acetyl-D-glucal ; 4) Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides : its stereoselectivity, and the use for kinetic resolution and asymmetrization ; 5) lipase-catalyzed enantiomeric resolution of ceramides.

新生物催化剂的筛选及其在生物活性化合物合成中的应用结果总结如下。1)(E)-3-氨基甲酰基-1-丙烯基硼酸在Suzuki-Miyaura偶联反应和酶反应组合中的关键作用：(3E，5E)-和(3E，5Z)-6-苯基-3，5-己二烯酸的合成；2)生物催化剂介导的高对映体富集型(R)-5-己内酯的高效制备；3)三-O-乙酰-D-醛的化学酶催化合成D-异丙三胺衍生物；4)红球菌IFO 15564-介导的脂环腈和酰胺的糖基化：其立体电性，并用于动力学拆分和不对称拆分；5)脂肪酶催化的金属陶瓷对映体拆分。

项目成果

Sugai, T.et al.: "Biocatalyst-mediated Efficient Preparation of Highly Enantiomerically Enriched(R)-5-Hexanolide" Synlett. 983-985 (1997)

Sugai, T.et al.：“生物催化剂介导的高度对映体富集(R)-5-己内酯的高效制备”Synlett。

Sugai,T.et al: "A Chemo-Enzymafic Synthesis of D-Allosamine Derivatlves from Tri-O-Acetyl-D-glucol" Bull.Chem.Soc.Jpn. 70. 2535-2540 (1997)

Sugai，T.et al：“从三-O-乙酰基-D-葡萄糖中化学酶合成 D-别糖胺衍生物”Bull.Chem.Soc.Jpn。

Sugai, T.et al.: "Pivotal Role of(E)--Carbamoyl-1-propenylboronic Acid in the Combination of Suzuki-Miyaura Coupling and Enzyme Reactions : Synthesis of (3E, 5E)- and (3E, 5Z)-6-Phenyl-3, 5-hexadienoic Acid" Chem.Lett.797-798 (1997)

Sugai, T.et al.：“(E)--氨基甲酰基-1-丙烯基硼酸在铃木-宫浦偶联和酶反应组合中的关键作用：(3E, 5E)- 和 (3E, 5Z)- 的合成

"Biocatalysis in Organic Synthesis : The Use of Nitrile-and Amide-Hydrolyzing Microorganisms" Biosci.Biotechnol. 61 Biochem.1419-1427 (1997)

“有机合成中的生物催化：腈和酰胺水解微生物的使用”Biosci.Biotechnol。

"Biocatalyst-mediated Efficient Preparation of Highly Enantiomerically Enriched (R) -5-Hexanolide" Synlett. 983-985 (1997)

“生物催化剂介导的高度对映体富集 (R)-5-己内酯的高效制备”Synlett。