L-2-acetamido-4-(hydroxymethylphosphinyl)butanoic acid | 125280-42-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-2-acetamido-4-(hydroxymethylphosphinyl)butanoic acid
• 英文别名: N-acethyl-L-glufosinate；N-acetylphosphinothricin；(S)-2-acetylamino-4-[(hydroxy)(methyl)]phosphinylbutanoic acid；N-Acetyl-L-phosphinothricin；(2S)-2-acetamido-4-[hydroxy(methyl)phosphoryl]butanoic acid
• CAS: 125280-42-4
• 化学式: C₇H₁₄NO₅P
• 分子量: 223.166
• InChiKey: VZVQOWUYAAWBCP-LURJTMIESA-N

物化性质

• 沸点：
  666.1±50.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-2-acetamido-4-(hydroxymethylphosphinyl)butanoic acid 、 盐酸 以99%的产率得到
  参考文献：
  名称：

  ZEISS, HANS-JOACHIM, J. ORG. CHEM., 56,(1991) N, C. 1783-1788

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-2-acetamido-4-(hydroxymethylphosphinyl)but-2-enoic acid 在 C₆₈H₇₂Cl₂Co₂P₄ 、 氢气 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、2.07 MPa 条件下， 反应 18.0h， 以100%的产率得到L-2-acetamido-4-(hydroxymethylphosphinyl)butanoic acid
  参考文献：
  名称：

  钴催化的不对称氢化制备旋光性氧膦基氨基丁酸类化合物的新方法

  摘要：

  本发明提供一种钴催化的不对称氢化制备旋光性氧膦基氨基丁酸类化合物的新方法，所述旋光性氧膦基氨基丁酸类化合物由通式(1)所示的化合物在钴盐—旋光性膦配体—锌催化体系下与氢气进行不对称氢化得到；所述钴盐—旋光性膦配体—锌催化体系由钴盐、旋光性膦化合物和锌粉组成；通式(1)所示的化合物的结构式为：通式(1)中，R1为C1～C4的烷基，R2为氢原子或C1～C4的烷基，R3为C1～C4的烷基、C1～C4的烷氧基、芳基、芳氧基或苄氧基，R4为氢原子或C1～C4的烷基。本发明可低成本、高效且高对映选择性地制备L‑2‑氨基‑4‑(羟甲基氧膦基)丁酸的重要中间体旋光性氧膦基氨基丁酸类化合物。

  公开号：

  CN109912648A

文献信息

• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINOPHOSPHINYLBUTANOIC ACIDS
  申请人：Minowa Nobuto

  公开号：US20090221851A1

  公开（公告）日：2009-09-03

  The present invention is a process for producing optically active aminophosphinylbutanoic acids represented by the formula (2) (in the formula (2), R 1 represents an alkyl group having 1 to 4 carbon atom(s), R 2 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), R 3 represents an alkyl group having 1 to 4 carbon atom(s), an alkoxy group having 1 to 4 carbon atom(s), an aryl group, an aryloxy group, or a benzyloxy group, and R 4 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s); and * represents an asymmetric carbon atom), wherein a compound represented by the formula (1) (in the formula (1), R 1 represents an alkyl group having 1 to 4 carbon atom(s), R 2 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), R 3 represents an alkyl group having 1 to 4 carbon atom(s), an alkoxy group having 1 to 4 carbon atom(s), an aryl group, an aryloxy group, or a benzyloxy group, and R 4 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s)) is asymmetrically hydrogenated in the presence of a ruthenium-optically active phosphine complex. With the process for the production, a compound useful in a herbicide such as L-AHPB can be produced with good efficiency and high asymmetric yield.

  本发明涉及一种制备光学活性氨基膦基丁酸的方法，其化学式为（2）（在化学式（2）中，R1代表具有1至4个碳原子的烷基，R2代表氢原子或具有1至4个碳原子的烷基，R3代表具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、芳基、芳氧基或苄氧基，R4代表氢原子或具有1至4个碳原子的烷基；*代表不对称碳原子），其中在钌-光学活性膦配合物的存在下，化学式（1）所表示的化合物（在化学式（1）中，R1代表具有1至4个碳原子的烷基，R2代表氢原子或具有1至4个碳原子的烷基，R3代表具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、芳基、芳氧基或苄氧基，R4代表氢原子或具有1至4个碳原子的烷基）进行不对称氢化。通过该制备方法，可以高效率、高对映选择性地制备出一种在除草剂中有用的化合物，如L-AHPB。
• [EN] L-GLUTAMATE DEHYDROGENASE MUTANT AND APPLICATION THEREOF<br/>[FR] MUTANT DE LA L-GLUTAMATE DEHYDROGÉNASE ET APPLICATION CORRESPONDANTE<br/>[ZH] 一种L-谷氨酸脱氢酶突变体及其应用
  申请人：ABIOCHEM BIOTECHNOLOGY CO LTD

  公开号：WO2019192505A1

  公开（公告）日：2019-10-10

  提供了一种L-谷氨酸脱氢酶突变体及其应用，所述突变体将SEQ ID NO.1所示的第166位氨基酸残基A，和/或第376位氨基酸残基V突变为亲水性或小位阻氨基酸残基，其应用为在L-氨基酸脱氢酶突变体、无机氨基供体和还原型辅酶NADPH的存在下，将2-氧代-4-(羟基甲基氧膦基)丁酸盐进行氨化反应，获得的L-草铵膦盐进行酸化反应制得L-草铵膦。所述L-谷氨酸脱氢酶突变体与野生型L-谷氨酸脱氢酶相比，在制备L-草铵膦时能够催化的底物浓度更高，从而提高酶的作用效率，降低反应的成本。
• Enantioselective synthesis of both enantiomers of phosphinothricin via asymmetric hydrogenation of .alpha.-acylamido acrylates
  作者：Hans Joachim Zeiss

  DOI：10.1021/jo00005a024

  日期：1991.3

  Both enantiomers of phosphinothricin (1), a naturally occuring amino acid that contains the unique methylphosphinate moiety, were prepared by asymmetric hydrogenation of alpha-acylamido acrylate precursors 7. L-1 and peptides containing L-1 are inhibitors of the enzyme glutamine synthetase (GS). Inhibition of GS is responsible for the antibiotical and herbicidal properties of these compounds. Synthesis of substrates 7 and parameters influencing the enantioselectivity are discussed. Substrate concentration and solvent polarity appear to have the most marked effects on enantiomeric excesses for a given catalyst system. Enantiomeric excesses reach 91 % for hydrogenations with (R,R)-NORPHOS- and (S,S)-CHIRAPHOS-derived catalysts.
• Spectroscopic characterization and mechanistic investigation of P-methyl transfer by a radical SAM enzyme from the marine bacterium Shewanella denitrificans OS217
  作者：Kylie D. Allen、Susan C. Wang

  DOI：10.1016/j.bbapap.2014.09.009

  日期：2014.12

  Natural products containing carbon-phosphorus bonds elicit important bioactivity in many organisms. L-Phosphinothricin contains the only known naturally-occurring carbon-phosphorus-carbon bond linkage. In actinomycetes, the cobalamin-dependent radical S-adenosyl-L-methionine (SAM) methyltransferase PhpK catalyzes the formation of the second C-P bond to generate the complete C-P-C linkage in phosphinothricin. Here we use electron paramagnetic resonance and nuclear magnetic resonance spectroscopies to characterize and demonstrate the activity of a cobalamin-dependent radical SAM methyltransferase denoted SD_1168 from Shewanella denitrificans OS217, a marine bacterium that has not been reported to synthesize phosphinothricin. Recombinant, refolded, and reconstituted SD_1168 binds a four-iron, four-sulfur cluster that interacts with SAM and cobalamin. In the presence of SAM, a reductant, and methylcobalamin, SD_1168 surprisingly catalyzes the P-methylation of N-acetyl-demethylphosphinothricin and demethylphosphinothricin to produce N-acetyl-phosphinothricin and phosphinothricin, respectively. In addition, this enzyme is active in the absence of methylcobalamin if the strong reductant titanium (III) citrate and hydroxocobalamin are provided. When incubated with [methyl-C-13] cobalamin and titanium citrate, both [methyl-C-13] and unlabeled N-acetylphosphinothricin are produced. Our results suggest that SD_1168 catalyzes P-methylation using radical SAM-dependent chemistry with cobalamin as a coenzyme. In light of recent genomic information, the discovery of this P-methyltransferase suggests that S. denitnficans produces a phosphinate natural product. (C) 2014 Elsevier B.V. All rights reserved.
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINOPHOSPHINYLBUTANOIC ACID
  申请人：Meiji Seika Pharma Co., Ltd.

  公开号：EP2060578B1

  公开（公告）日：2014-04-09