| 李欢欢,段培高,黄雅文,申倩倩,张武元.光酶级联一锅法合成手性脂肪胺[J].分子催化,2023,37(4):323-330 |
| 光酶级联一锅法合成手性脂肪胺 |
| One Pot Photoenzymatic Cascades to Synthesize Chiral Aliphatic Amines |
| 投稿时间：2023-04-26 修订日期：2023-06-04 |
| DOI：10.16084/j.issn1001-3555.2023.04.001 |
| 中文关键词: 光-酶级联 脂肪胺 转氨酶 生物催化 绿色合成 |
| 英文关键词:photobiocatalysis aliphatic amines transaminase biocatalysis green synthesis |
| 基金项目:中国自然科学基金(No.32171253)和天津合成生物技术创新能力行动项目(No.TSBICIP-CXRC-032)资助 |
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| 中文摘要: |
| 对映体脂肪胺在有机合成与化工领域具有广泛的应用, 但其主要依赖于金属催化获得. 我们设计了一种光催化与酶催化级联催化的合成方法, 由脂肪醇出发合成手性脂肪胺. 通过筛选, 发现9-芴酮在可见光激发下可高效催化脂肪醇氧化为脂肪酮, 后者作为反应中间体被转氨酶在胺供体存在下经转氨反应合成手性胺. 在一锅法条件下, 该级联方法转化率可达99%, 目标产物的光学纯度>99%. 此外, 该光催化体系可分别与手性互补的转氨酶级联, 进而获得手性反转的脂肪胺产物. 该光酶级联催化方法充分结合了光催化的高效率与酶催化的立体选择性优势, 为手性脂肪胺类分子的合成提供了一种新型合成方法. |
| 英文摘要: |
| Enantiomerically enriched fatty amines have widespread application in organic synthesis and chemical engineering, but today their production mainly relies on traditional metal catalysis. This paper presents a novel method by combining photocatalysis and biocatalysis to synthesize chiral fatty amines from fatty alcohols. Through screening, we discovered that 9-fluorenone efficiently catalyzes the oxidation of fatty alcohols to fatty ketones under visible light irradiation. The ketone intermediates are then converted into chiral amines by transaminase in the presence of amine donors. This one-pot cascade achieves a conversion of 99% and an optical purity of >99% for the target products. In addition, this photo-biocatalytic system can be expanded to transaminases to obtain fatty amines with complementary chirality. Overall, the photo-biocatalytic cascade effectively combines the high efficiency of photocatalysis with the stereoselective advantages of enzymes, offering a new synthetic route for chiral fatty amine compounds. |
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