Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors

Duc Hai Dao; Yasushi Kawai; Kouichi Hida; Sander Hornes; Kaoru Nakamura; Atsuyoshi Ohno; Mutsuo Okamura; Takeshi Akasaka

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Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors

机译：微生物减少中的立体化学控制。 30.还原2-氧代-4-苯基丁酸烷基酯作为血管紧张素转化酶（ACE）抑制剂的前体

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Alkyl 2-oxo-4-phenylbutyrates are reduced to the corresponding alkyl (R)-2-hydroxy-4-phenylbutyrates, versatile chiral building blocks in organic synthesis, in high chemical yield (80-90%) with excellent stereoselectivity (>90%ee). The reaction has been run in aqueous diethyl ether at 30 ℃ for 24 h under the catalysis of bakers' yeast (Saccharomyces cerevisiae) which was preincubated for 6 h in the presence of phenacyl chloride. The amount of water in the medium should be controlled strictly not to exceed 0.8 mL (g yeast)~(-1).

机译：将2-氧代-4-苯基丁酸烷基酯还原为相应的烷基（R）-2-羟基-4-苯基丁酸烷基酯，这是有机合成中通用的手性结构单元，化学产率高（80-90％），立体选择性优异（> 90）％ee）。该反应已在面包酵母（啤酒酵母）的催化下于30℃的乙醚水溶液中进行24小时，该酵母在苯甲酰氯存在下预孵育6小时。培养基中的水量应严格控制在不超过0.8 mL（克酵母）〜（-1）。

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《Bulletin of the Chemical Society of Japan》 |1998年第2期|共8页
作者
Duc Hai Dao; Yasushi Kawai; Kouichi Hida; Sander Hornes; Kaoru Nakamura; Atsuyoshi Ohno; Mutsuo Okamura; Takeshi Akasaka;
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正文语种 eng
中图分类化学;化学工业;
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1. Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors [J] . Duc Hai Dao, Yasushi Kawai, Kouichi Hida, Bulletin of the Chemical Society of Japan . 1998,第2期

机译：微生物减少中的立体化学控制。 30.还原2-氧代-4-苯基丁酸烷基酯作为血管紧张素转化酶（ACE）抑制剂的前体
2. A 16-week, randomized, double-blind, placebo-controlled, crossover trial to quantify the combined effect of an angiotensin-converting enzyme inhibitor and a beta-blocker on blood pressure reduction. [J] . Wald DS, Law M, Mills S, Clinical therapeutics . 2008,第11期

机译：一个16周，随机的双盲，安慰剂控制的交叉试验，用于量化血管紧张素转换酶抑制剂和β-阻滞剂对血压降低的综合作用。
3. Cardiovascular Outcomes and Angiotensin Converting Enzyme Inhibitors: Beyond Blood Pressure Control Editorial to: “Secondary Prevention of Coronary Disease with ACE Inhibition—Does Blood Pressure Reduction with Perindopril Explain the Benefits in EUROPA?” by Remme et al. [J] . Anil Verma, Hector O. Ventura Cardiovascular Drugs and Therapy . 2009,第2期

机译：心血管结果和血管紧张素转换酶抑制剂：超越血压控制社论：“通过ACE抑制对冠心病的二次预防-培哚普利降低血压能说明EUROPA的益处吗？”由Remme等人撰写。
4. Synthesis of the first highly potent inhibitor of the three vasopeptidases:endothelin converting enzyme (ECE),angiotensin converting enzyme (ACE) and neprilysin (NEP) [C] . Nicolas Inguimbert, Herve Poras, Pascale Coric, European Peptide Symposium . 2002

机译：三种血管肽酶的第一高效抑制剂的合成：内皮素转化酶（ECE），血管紧张素转化酶（ACE）和Neplysin（NEP）
5. Utilization of Vasopressin as a First Line Response to Perioperative Hypotension in the Patient on Angiotensin Receptor Antagonists and Angiotensin Converting Enzyme Inhibitors [D] . Buckley, Emily A. 2015

机译：利用血管加压素作为对围手术期低血压患者的血管紧张素受体拮抗剂和血管紧张素转化酶抑制剂的一线反应
6. Angiotensin-Converting Enzyme Inhibitors (ACEIs) and Angiotensin-Receptor Blockers (ARBs) in Patients at High Risk of Cardiovascular Events: A Meta-Analysis of 10 Randomised Placebo-Controlled Trials [O] . Hean Teik Ong, Loke Meng Ong, Jacqueline Judith Ho 2013

机译：心血管事件高风险患者的血管紧张素转换酶抑制剂（ACEIs）和血管紧张素受体阻滞剂（ARBs）：对10个随机安慰剂对照试验的荟萃分析
7. Stereochemical Control in Microbial Reduction. 9. Diastereoselective Reduction of 2-Alkyl-3-oxobutanoate with Bakers’ Yeast [O] . Kaoru Nakamura, Takehiko Miyai, Ashish Nagar, 1989

机译：微生物减少的立体化学控制。 9.用Bakers的酵母进行2-烷基-3-氧脱酸酯的非对映选择性减少
8. Comparative Effectiveness of Angiotensin-Converting Enzyme Inhibitors (ACEls) and Angiotensin II Receptor Antagonists (ARBs) for Treating Essential Hypertension. Comparative Effectiveness Review, Number 10 [R] . Matchar, D. B., McCrory, D. C., Orlando, L. A., 2007

机译：血管紧张素转换酶抑制剂（aCEls）和血管紧张素II受体拮抗剂（aRBs）治疗原发性高血压的疗效比较。比较效力评估，第10号

Stereochemical Control in Microbial Reduction. 30. Reduction of Alkyl 2-Oxo-4-phenylbutyrate as Precursors of Angiotensin Converting Enzyme (ACE) Inhibitors

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