(R)-3-fluorolactic acid | 3130-92-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (R)-3-fluorolactic acid
• 英文别名: Propanoic acid, 3-fluoro-2-hydroxy-, (R)-；(2R)-3-fluoro-2-hydroxypropanoic acid
• CAS: 3130-92-5
• 化学式: C₃H₅FO₃
• 分子量: 108.069
• InChiKey: UYIAUFVPRSSBGY-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (R)-3-fluorolactic acid 生成 (R)-3-fluorolactic acid methyl ester
  参考文献：
  名称：

  Enzymatic laboratory scale production of homochiral (R)-3-fluorolactic acid methyl ester via enantiospecific reduction of sodium fluoropyruvate catalyzed by rabbit muscle l-lactate dehydrogenase (l-LDH)

  摘要：

  In the present work a simple laboratory procedure for the synthesis of (R)3-Fluorolactic Methyl Ester(1) is described A coupled enzymatic system formed by rabbit muscle L-lactate dehydrogenase (L-LDH), horse liver alcohol dehydrogenase (HLADH), fluoropyruvic acid sodium salt, NAD(+) and cis-1,2-bis(hydroxymethyl)cyclohexane were found to be very effective for production of(1) in 80% overall yield and ee > 99%. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00131-0
• 作为产物：
  描述：

  β-氟丙酮酸钠盐 在 phosphate buffer 、 cis-1,2-cyclohexanedimethanol 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (R)-3-fluorolactic acid
  参考文献：
  名称：

  Enzymatic laboratory scale production of homochiral (R)-3-fluorolactic acid methyl ester via enantiospecific reduction of sodium fluoropyruvate catalyzed by rabbit muscle l-lactate dehydrogenase (l-LDH)

  摘要：

  In the present work a simple laboratory procedure for the synthesis of (R)3-Fluorolactic Methyl Ester(1) is described A coupled enzymatic system formed by rabbit muscle L-lactate dehydrogenase (L-LDH), horse liver alcohol dehydrogenase (HLADH), fluoropyruvic acid sodium salt, NAD(+) and cis-1,2-bis(hydroxymethyl)cyclohexane were found to be very effective for production of(1) in 80% overall yield and ee > 99%. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00131-0

文献信息

• Kinetic aspects involved in the simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid
  作者：Luciana P.B. Gonçalves、O.A.C. Antunes、Gerson F. Pinto、Enrique G. Oestreicher

  DOI：10.1016/j.jfluchem.2003.08.009

  日期：2003.12

  enzymatic system for the simultaneous synthesis of (S)-3-fluoroalanine (1a) and (R)-3-fluorolactic acid (3) with l-ALADH and l-lactate dehydrogenase using rac-1 and NAD+. Analysis of isolated products revealed 1a in 60% yield and 86% ee and 3 in 80% yield and over 99% ee. Compounds 1a and 3 represent chiral building blocks for the synthesis of several products with pharmacological activity. The presence

  在存在和不存在产物的情况下，通过初始速率实验，研究了由I-丙氨酸脱氢酶（I-ALADH）催化的rac -3-氟丙氨酸（rac -1）的脱氨基氧化。获得了反应动力学参数的估计。反应机理是顺序有序的BiTer机理，其被过量的（S）-3-氟丙氨酸抑制。这项动力学研究是开发双酶系统的基础，该酶系统可同时用L-ALADH和L-乳酸脱氢酶合成（S）-3-氟丙氨酸（1a）和（R）-3-氟乳酸（3）。使用rac -1和NAD +。分离产物的分析表明，产率为60％，ee为86％的1a和产率为99％ee的80％的3。化合物1a和3代表用于合成几种具有药理活性的产物的手性结构单元。底物中氟原子的存在导致其在酶的活性位点更好的相互作用。
• Enantioselective oxidation of 1,2-diols to L-.alpha.-hydroxy acids using co-immobilized alcohol and aldehyde dehydrogenases as catalysts
  作者：Chi Huey Wong、Jose R. Matos

  DOI：10.1021/jo00211a046

  日期：1985.5
• Thermodynamics and Kinetic Aspects Involved in the Enzymatic Resolution of (<i>R,S</i>)-3-Fluoroalanine in a Coupled System of Redox Reactions Catalyzed by Dehydrogenases
  作者：Luciana P. B. Gonçalves、O. A. C. Antunes、Enrique G. Oestreicher

  DOI：10.1021/op060027o

  日期：2006.5.1

  Two systems of redox enzymatic reactions were tested, looking forward to the preparation of (S)-3-fluoroalanine, a potent antibiotic, by kinetic resolution of rac-3-fluoroalanine. This starting material was the main substrate for the deaminative oxidation reaction catalyzed by L-alanine dehydrogenase (L-AlaDH) in the presence of NAD(+). One system was formed by coupling this reaction ( main reaction) to the reduction of 3-fluoropyruvate ( a cascade system) produced in the main reaction catalyzed by L-lactate dehydrogenase (L-LDH) in the presence of NADH, also formed in the main reaction. This system, that was able to achieve 92% of conversion, allows the accumulation of NH4+, one of the secondary products of the main reaction. The other coupled redox system involved the coupling to the L-AlaDH reaction to the aminative reduction reaction of alpha-ketoglutarate in the presence of NADH and NH4+ ( both side products of the main reaction) catalyzed by L-glutamate dehydrogenase (L-GluDH), that allows accumulation of 3-fluoropyruvate. With this system, the extent of the reaction in the coupled system was only 22%. This big difference in the efficiency of both systems was identified as being the result of a different potency of the products that accumulates in both systems, acting as inhibitors of L-AlaDH. It was demonstrated that 3-fluoropyruvate is a much stronger inhibitor of L-AlaDH than NH4+. This fact, and not thermodynamic considerations, explains the results obtained with both systems.
• Simultaneous enzymatic synthesis of ( S )-3-fluoroalanine and ( R )-3-fluorolactic acid
  作者：L.P.B Gonçalves、O.A.C Antunes、G.F Pinto、E.G Oestreicher

  DOI：10.1016/s0957-4166(00)00096-3

  日期：2000.4

  A coupled enzymatic system for the simultaneous synthesis of (S)-3-fluoroalanine (1a) and (R)-3-fluorolactic acid (3) with L-alanine dehydrogenase (L-AlaDH) from Bacillus subtilis and rabbit muscle L-lactate dehydrogenase (L-LDH) using rac-1 and NAD(+) is described. Analysis of isolated products of the laboratory preparative scale process revealed la in 60% yield and 88% ee and 3 in 80% yield and over 99% ee. The compounds la and 3 represent chiral building blocks for the synthesis of several products with pharmacological activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Enzymatic laboratory scale production of homochiral (R)-3-fluorolactic acid methyl ester via enantiospecific reduction of sodium fluoropyruvate catalyzed by rabbit muscle l-lactate dehydrogenase (l-LDH)
  作者：L.P.B. Gonçalves、O.A.C. Antunes、G.F. Pinto、E.G. Oestreicher

  DOI：10.1016/0957-4166(96)00131-0

  日期：1996.5

  In the present work a simple laboratory procedure for the synthesis of (R)3-Fluorolactic Methyl Ester(1) is described A coupled enzymatic system formed by rabbit muscle L-lactate dehydrogenase (L-LDH), horse liver alcohol dehydrogenase (HLADH), fluoropyruvic acid sodium salt, NAD(+) and cis-1,2-bis(hydroxymethyl)cyclohexane were found to be very effective for production of(1) in 80% overall yield and ee > 99%. Copyright (C) 1996 Elsevier Science Ltd