Thiamin-Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C-C Bond Formation

Martina Pohl; Bettina Lingen; Michael Muller

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Thiamin-Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C-C Bond Formation

机译：硫胺素-二磷酸依赖性酶：不对称C-C键形成的新方面。

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Starting from a thorough investigation of mechanistic aspects of ThDP-dependent (ThDP = thiamin diphosphate) enzymes in combination with mutagenesis studies and a detailed substrate screening, new general synthetic methods have been developed based on Umpolung reactions by thiamin catalysis. A selective donor-acceptor concept was established leading to the first asymmetric cross-benzoin condensation, and a kinetic racemic resolution through C-C bond cleavage was developed. With these tools and in combination with protein engineering, we approached the synthesis of new chiral building blocks on a preparative scale. An outlook is given with respect to the potential of other ThDP-dependent enzymes as catalysts in asymmetric synthesis.

机译：从彻底研究ThDP依赖性（ThDP =硫胺素二磷酸）酶的机械方面，并结合诱变研究和详细的底物筛选开始，基于硫胺素催化的Umpolung反应，开发了新的通用合成方法。建立了选择性的供体-受体概念，导致了第一次不对称的交叉安息香缩合，并开发了通过C-C键断裂形成的动力学外消旋体。通过这些工具，再结合蛋白质工程，我们以制备规模进行了新手性构件的合成。展望了其他不依赖ThDP的酶作为不对称合成催化剂的潜力。

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《Chemistry: A European journal》 |2002年第23期|共7页
作者
Martina Pohl; Bettina Lingen; Michael Muller;
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正文语种 eng
中图分类化学;应用化学;
关键词
cleavage reactions; enzyme catalysis; protein engineering; umpolung;

机译：裂解反应;酶催化;蛋白质工程;蛋白修饰;

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1. Thiamin-Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C-C Bond Formation [J] . Martina Pohl, Bettina Lingen, Michael Muller Chemistry: A European journal . 2002,第23期

机译：硫胺素-二磷酸依赖性酶：不对称C-C键形成的新方面。
2. TCA cycle involved enzymes SucA and Kgd, as well as MenD: Efficient biocatalysts for asymmetric C-C bond formation [J] . Beigi M., Waltzer S., Fries A., Organic letters . 2013,第3期

机译：TCA周期涉及酶SucA和Kgd以及MenD：用于不对称C-C键形成的高效生物催化剂
3. Branched-Chain Keto Acid Decarboxylase from Lactococcus lactis(KdcA),a Valuable Thiamine Diphosphate-Dependent Enzyme for Asymmetric C-C Bond Formation [J] . Dorte Gocke, Cong Luan Nguyen, Martina Pohl Advanced synthesis & catalysis . 2007,第8a9期

机译：乳酸乳球菌（KdcA）的支链酮酸脱羧酶，一种重要的硫胺素二磷酸依赖性酶，可形成不对称的C-C键。
4. Catalytic Asymmetric C-C Bond Formation with Chiral Ruthenium Amido Complexes [C] . Masahito Watanabe, Hui Wang, Ayako Ikagawa, Symposium on Organometallic Chemistry . 2004

机译：催化不对称C-C键形成，具有手性钌酰胺络合物
5. I. Enantioselective total synthesis of quinine and quinidine. II. Thiourea-catalyzed enantioselective C-C bond-forming reactions. a. Catalytic asymmetric N-acyliminium ion cyclizations. b. Catalytic asymmetric aza-Baylis-Hillman reactions [D] . Raheem, Izzat Tiedje 2008

机译：I.奎宁和奎尼丁的对映选择性全合成。二。硫脲催化的对映选择性C-C键形成反应。一个。催化不对称N-酰亚胺离子环化。 b。催化不对称氮杂-Baylis-Hillman反应
6. Efficient Access to Multifunctional Trifluoromethyl Alcohols via Base-free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides [O] . Andrea M. Cook, Christian Wolf -1

机译：通过无碱催化不对称C-C键与末端酰胺形成多功能三氟甲基醇
7. Studies on the C-C Bond Formation Methods Based on the Activation of Secondary Amides and the Asymmetric Total Synthesis of Cylindricine D [O] . 黄应红 2016

机译：基于仲酰胺活化和Cylindricine D不对称全合成的C-C键形成方法研究

Thiamin-Diphosphate-Dependent Enzymes: New Aspects of Asymmetric C-C Bond Formation

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