methyl acetyl-D-methioninate

• 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: methyl acetyl-D-methioninate
• 英文别名: N-acetyl-D-methionine methyl ester；N-Ac-Met-OMe；Methyl (2R)-2-acetamido-4-(methylsulfanyl)butanoate；methyl (2R)-2-acetamido-4-methylsulfanylbutanoate
• 化学式: C₈H₁₅NO₃S
• 分子量: 205.278
• InChiKey: YVMKSJIMTATAAS-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl acetyl-D-methioninate 在 盐酸 、 四丁基高氯酸铵 、 氧气 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以46%的产率得到methyl (2R)-2-acetamido-4-(methylsulfinyl)butanoate
  参考文献：
  名称：

  在连续流微反应器中对硫化物和硫醇进行环境友好的选择性电化学氧化

  摘要：

  提出了在商业上可获得的连续流微反应器中硫醚和硫醇的实用且对环境无害的电化学氧化。水被用作氧气源以实现氧化过程。氧化反应在所有情况下都使用相同的试剂，并且选择性仅由施加的电势控制。该方法具有广泛的应用范围和良好的官能团相容性，可以使用各种亚砜（15个实例），砜（15个实例）和二硫化物（6个实例）。连续流的使用允许快速评估最佳反应参数（例如停留时间，施加的电压），以避免传质和传热限制，并扩大电化学规模。

  DOI：

  10.1039/c7gc01973d
• 作为产物：
  描述：

  N-乙酰-DL-蛋氨酸 在 氯化亚砜 、 Acylase I on Eupergit C 、 水 作用下， 反应 1.5h， 生成 methyl acetyl-D-methioninate
  参考文献：
  名称：

  Use of enantio-, chemo- and regioselectivity of acylase I. Resolution of polycarboxylic acid esters

  摘要：

  Acylase I was used to catalyze the enantioselective butanolysis of trimethyl 2-[(carboxymethyl)oxy]succinate (E=30) and N-carboxymethylaspartate (E=9) exclusively at the most sterically hindered of the three ester group's (the position alpha to the asymmetric centre). Gram-scale resolution allowed the preparation of the less reactive trimethyl (S)-2-[(carboxymethyl)oxy]succinate (96% e.e.), that of the (R)-butyldimethyl regioisomer (78% e.e.) at 55% conversion and finally the preparation of the corresponding trisodium carboxylate by saponification. Acylase I was shown to transform (+/-)-methyl N-acetylmethionine and (+/-)-valine to the corresponding (S)-amino acids through ester hydrolysis-N-acetyl transfer sequence with absolute chemo- and enantioselectivity. Butanolysis of methyl N-acetylmethionine stopped in the formation of the butyl ester (E=12), the valine derivative being totally unreactive. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00362-7

文献信息

• Integrating hydrogen production with anodic selective oxidation of sulfides over a CoFe layered double hydroxide electrode
  作者：Lina Ma、Hua Zhou、Ming Xu、Peipei Hao、Xianggui Kong、Haohong Duan

  DOI：10.1039/d0sc05499b

  日期：——

  cathodic H2 productivity. This protocol displays high activity (85–96% yields), catalyst stability (10 cycles), and generality (12 examples) in selective sulfide oxidation. We demonstrate its applicability in the synthesis of four important pharmaceutical related sulfoxide compounds with scalability (up to 1.79 g). X-ray spectroscopy investigations reveal that the CoFe-LDH material evolved into amorphous

  用氧化反应代替缓慢的析氧反应 (OER) 来合成复杂的药物分子并结合增强的析氢反应 (HER) 是非常有吸引力的，但它很少被探索。在这里，我们报告了一种电化学方案，用于在水性-MeCN 电解质中的 CoFe 层状双氢氧化物 (CoFe-LDH) 阳极上将硫化物选择性氧化为亚砜，再加上 2 倍促进的阴极 H 2生产率。该协议在选择性硫化物氧化中表现出高活性（85–96% 产率）、催化剂稳定性（10 个循环）和通用性（12 个示例）。我们证明了它在合成四种重要的药物相关亚砜化合物中的适用性，具有可扩展性（高达 1.79 g）。X 射线光谱研究表明，CoFe-LDH 材料在催化条件下演变为无定形 CoFe-羟基氧化物。这项工作可能为有价值药物的可持续有机合成以及 H 2生产铺平道路。
• Lipase activity of Lecitase® Ultra: characterization and applications in enantioselective reactions
  作者：Mithilesh Kumar Mishra、Thenkrishnan Kumaraguru、Gurrala Sheelu、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2009.11.012

  日期：2009.12

  The general properties of Lecitase (R) Ultra, a phospholipase manufactured and marketed by Novozymes, Denmark, have been studied after purification by ultrafiltration. The enzyme has a molecular mass of 35 KD, pH-optimum of 8.5, and appears to possess a single active site which exhibits both the lipase and phospholipase activities that increase in the presence of Ca2+ and Mg2+ ions. The enzyme is inhibited by heavy metal ions and surfactants, and does not accept p-nitrophenyl acetate and glycerol triacetate. Substrates, such as glycerol tributyrate and p-nitrophenyl palmitate, esters of N-acetyl-alpha-amino acids and alpha-hydroxy acids are readily accepted. Amino acids with aliphatic residues, such as alanine, isoleucine, and methionine, are hydrolyzed with high enantioselectivity for the L-enantiomer (E > 100), but amino acids with aromatic residues such as phenylalanine and phenylglycine, and esters of alpha-hydroxy acids are hydrolyzed with low enantioselectivity (E = 1-5). Immobilization of the enzyme in a gelatin matrix (gelozyme) leads to a marginal improvement in the enantioselectivity for these substrates. However, a dramatic improvement in enantioselectivity is observed for ethyl 2-hydroxy-4-oxo-4-phenylbutyrate (E value increases from 4.5 to 19.5 with S-selectivity). Similarly, glycidate esters, such as ethyl trans-(+/-)-3-phenyl glycidate and methyl trans-(+/-)-3-(4-methoxyphenyl) glycidate, are selectively hydrolyzed with a remarkable selectivity towards the (2S,3R)-enantiomer providing unreacted (2R,3S)-glycidate esters (ee >99%, conversion 52-55%) by the immobilized enzyme. (C) 2009 Elsevier Ltd. All rights reserved.
• CALMES, M.;DAUNIS, J.;JACQUIER, R.;VERDUCCI, J., TETRAHEDRON, 43,(1987) N 10, 2285-2292
  作者：CALMES, M.、DAUNIS, J.、JACQUIER, R.、VERDUCCI, J.

  DOI：——

  日期：——
• PROCESS FOR PRODUCING N-ACYL-D-PHENYLALANINE ESTER
  申请人：ETHYL CORPORATION

  公开号：EP0028251A1

  公开（公告）日：1981-05-13
• EP0028251A4
  申请人：——

  公开号：EP0028251A4

  公开（公告）日：1981-03-27