Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate

Mihyang Kim; E. Neil G. Marsh; Soo-Un Kim; Jachong Han

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Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate

机译：通过THD还原酶将（3S，4R）-四氢黄豆苷元转变为（3S）-Equol：涉及自由基中间体的拟议机制

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To elucidate the mechanism of (3S)-equol biosynthesis, (2,3,4-d_3)-trans-THD was synthesized and converted to (3S)-equol by THD reductase in Eggerthella strain Julong 732. The position of the deuterium atoms in (3S)-equol was determined by~1 H NMR and ~2H NMR spectroscopy, and the product was identified as (2,3,4_α-d_3)-(3S)-equol. All the deuterium atoms were retained, while the OH group at C-4 was replaced by a hydrogen atom with retention of configuration. To explain the deuterium retention in this stereospecific reduction, we propose a mechanism involving radical intermediates.

机译：为了阐明（3S）-雌马酚生物合成的机理，合成了（2,3,4-d_3）-反式-THD，并通过THD还原酶在Eggerthella株Julong 732中转化为（3S）-雌马酚。氘原子的位置通过〜1 H NMR和〜2 H NMR光谱法测定（3S）-雌马酚中的化合物，鉴定为（2,3,4_α-d_3）-（3S）-雌马酚。所有氘原子均被保留，而C-4处的OH基团被保留结构的氢原子取代。为了解释这种立体定向还原中的氘保留，我们提出了一种涉及自由基中间体的机制。

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《Biochemistry》 |2010年第26期|共6页
作者
Mihyang Kim; E. Neil G. Marsh; Soo-Un Kim; Jachong Han;
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正文语种 eng
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Conversion; Reductase; Intermediate;

机译：转化;还原酶;中间体;

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1. Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate [J] . Mihyang Kim E. Neil G. Marsh Soo-Un Kim and Jaehong Han Biochemistry . 2010,第26期

机译：通过THD还原酶将（3S，4R）-四氢黄豆苷元转换为（3S）-Equol：涉及自由基中间体的拟议机制
2. Synthesis of (3S,4R)-4-benzylamino-3-methoxypiperidine, an important intermediate for (3S,4R)-Cisapride [J] . Shirode NM, Likhite AP, Gumaste VK, Tetrahedron . 2008,第30a31期

机译：（3S，4R）-4-苄氨基-3-甲氧基哌啶的合成，这是（3S，4R）-Cisapride的重要中间体
3. Mechanism of the Forbidden [3s,5s]-Sigmatrpic Shift: orbital Symmetry Influences Stepwise Mechanisms Involving Diradical Intermediates [J] . Andrew G. Leach, Saron Catak, K.N. Houk Chemistry: A European journal . 2002,第6期

机译：[3s，5s] -Sigmatrpic移位的机制：轨道对称性影响涉及双自由基中间体的逐步机制。
4. Synthesis and crystal structure of 1-(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyI)tetrariyclrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione [C] . Wei Li, Qiang Xiao, Ruchun Yang International Conference on Chemical Engineering, Metallurgical Engineering and Metallic Materials . 2014

机译：合成和晶体结构1-（2R，3S，4R，5R）-3-氟-4-羟基-5-（羟甲乙基）四-5-碘嘧啶-2-基-2,4（1H，3H） - 迪奥牛
5. (3R,4S),(3S,4R) and (3R,4R),(3S,4S)-4-amino-5-fluoro-3-phenyl pentanoic acids as mechanism-based inactivators of 4-aminobutyric acid aminotransferase [D] . Nanavati, Shrenik M. 1988

机译：（3R，4S），（3S，4R）和（3R，4R），（3S，4S）-4-氨基-5-氟-3-苯基戊酸是基于机制的4-氨基丁酸氨基转移酶灭活剂
6. Stereospecific Biotransformation of Dihydrodaidzein into (3S)-Equol by the Human Intestinal Bacterium Eggerthella Strain Julong 732 [O] . Mihyang Kim, Su-Il Kim, Jaehong Han, 2009

机译：二氢黄豆苷元的人肠细菌埃格氏菌株朱龙732的立体定向生物转化为（3S）-紫杉醇。
7. Further Structural Exploration of Trisubstituted Asymmetric Pyran Derivatives (2S, 4R, 5R)-2-Benzhydryl-5-benzylamino-tetrahydropyran-4-ol and Their Corresponding Disubstituted (3S, 6S) Pyran Derivatives: A Proposed Pharmacophore Model for High-Affinity Interaction with the Dopamine, Serotonin, and Norepinephrine Transporters [O] . -1

机译：Trisubstuted不对称吡喃衍生物（2s，4r，5r）-2-苯甲酰-5-苄基氨基 - 四氢吡喃-4-醇及其相应二取代（3S，6s）吡喃衍生物的进一步结构探索：一种用于高亲和力相互作用的提出的药物模型用多巴胺，血清素和去甲肾上腺素转运蛋白

Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate

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