Preparation of Optically Active γ- and δ-Lactones by Microbiological Reduction of the Corresponding Keto Acids

G. Tuynenburg Muys; B. Van Der Ven; A. P. De Jonge

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Preparation of Optically Active γ- and δ-Lactones by Microbiological Reduction of the Corresponding Keto Acids

机译：通过微生物还原相应的酮酸制备旋光性γ-和δ-内酯

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It was found, by means of simple screening methods, that several yeasts (Saccharomyces and Candida), molds (Cladosporium), and bacteria (Sarcina) are able to reduce keto acids to hydroxy acids, which are easily converted into lactones. Chemical analysis showed that some of the microorganisms (Saccharomyces and Candida) produce dextrorotatory lactones and others (Cladosporium and Sarcina) produce levorotatory lactones. High yields of dextrorotatory (both γ- and δ-lactones) were obtained by using Saccharomyces cerevisiae. The physical properties of the carefully distilled lactones obtained indicated high purity and high optical purity.

机译：通过简单的筛选方法发现，几种酵母菌（酵母菌和念珠菌），霉菌（剑孢菌）和细菌（Sa菌）能够将酮酸还原为羟酸，而羟酸很容易转化为内酯。化学分析表明，某些微生物（酿酒酵母和念珠菌）产生右旋内酯，而其他微生物（Cladosporium和Sarcina）产生左旋内酯。通过使用酿酒酵母获得了高产率的右旋（γ-和δ-内酯）。所获得的精心蒸馏的内酯的物理性质表明其具有高纯度和高光学纯度。

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《Applied Microbiology》 |1963年第5期|共5页
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G. Tuynenburg Muys; B. Van Der Ven; A. P. De Jonge;
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1. Barbier-Type Reactions of Cyclic Acid Anhydrides and Keto Acids Mediated by an SmI_2/(NiI_2-Catalytic) System - Preparation of Disubstituted Lactones [J] . Fouzia Machrouhi, Elena Parlea, Jean-Louis Namy European journal of organic chemistry . 1998,第11期

机译：SmI_2 /（NiI_2-催化）体系介导的环酸酐和酮酸的Barbier型反应-双取代内酯的制备
2. (HMe2SiCH2)(2): A Useful Reagent for B(C6F5)(3)-Catalyzed Reduction-Lactonization of Keto Acids: Concise Syntheses of (-)-cis-Whisky and (-)-cis-Cognac Lactones [J] . Xie Hengmu, Lu Ji, Gui Yingying, Synlett . 2017,第18期

机译：（HME2SICH2）（2）：用于B（C6F5）（3）的有用试剂 - 催化酸酸还原 - 酮酸的缺点：（ - ） - 顺式威士忌和（ - ） - CIS-Cognac内酯的简明合成
3. Complementary Diastereoselective Reduction of Cyclic γ-Keto Acids: Efficient Access to Trisubsituted γ-Lactones [J] . Eric A. Bercot, David E. Kindrachuk, Tomislav Rovis Organic letters . 2005,第1期

机译：环状γ-酮酸的非对映选择性互补还原：有效获得三取代的γ-内酯
4. Catalytic Asymmetric Synthesis of α-Amino Acid Derivatives: Approaches toward Green Sustainable Methodology for Preparation of Optically Active Amino Acids [C] . Yasuhiro Yamashita, Shu Kobayashi Asymmetric synthesis and application of α-amino acids . 2007

机译：催化不对称合成α-氨基酸衍生物：绿色可持续方法制备光学活性氨基酸的方法
5. Alpha-keto acids, alpha-keto esters, diketopiperazines, 2,5-bis-alkoxy-3,6-dihydropyrazines, and morpholinediones as potential amino acid bioprecursors for delivery of an AMPA antagonist to the central nervous system [D] . Danthi, Satyavijayan Narasimhan. 1997

机译：α-酮酸，α-酮酯，二酮哌嗪，2,5-双烷氧基-3,6-二氢吡嗪和吗啉二酮是潜在的氨基酸生物前体，可将AMPA拮抗剂递送至中枢神经系统
6. Preparation of Optically Active γ- and δ-Lactones by Microbiological Reduction of the Corresponding Keto Acids [O] . G. Tuynenburg Muys, B. Van Der Ven, A. P. De Jonge 1963

机译：通过微生物还原相应的酮酸制备旋光性γ-和δ-内酯
7. Preparation of Optically Active γ- and δ-Lactones by Microbiological Reduction of the Corresponding Keto Acids [O] . G. Tuynenburg Muys, B. Van Der Ven, A. P. De Jonge 1963

机译：通过微生物减少对应的酮酸制备光学活性γ-和δ-内酯

Preparation of Optically Active γ- and δ-Lactones by Microbiological Reduction of the Corresponding Keto Acids

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