N-phenylacetyl-D-Ser methyl ester

• 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: N-phenylacetyl-D-Ser methyl ester
• 英文别名: methyl (2R)-3-hydroxy-2-[(2-phenylacetyl)amino]propanoate
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: LEXXWUZQWCUIIP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-丝氨酸甲酯 、 苯乙酸甲酯 在 penicillin-G amidase from E_. coli 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-phenylacetyl-D-Ser methyl ester
  参考文献：
  名称：

  Quantitative enzymatic protection of d-amino acid methyl esters by exploiting ‘relaxed’ enantioselectivity of penicillin-G amidase in organic solvent

  摘要：

  The lower enantio selectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various D-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.153

文献信息

• Amide-Bond Syntheses Catalyzed by Penicillin Acylase
  作者：Antonio Pessina、Peter Lüthi、Pier Luigi Luisi、Jiri Prenosil、You-Shang Zhang

  DOI：10.1002/hlca.19880710317

  日期：1988.5.4

  both in H2O solution and in organic solvents containing reverse micelles. The specificity of the reaction is rather high on the side of the acyl component, practically only phenylacetic acid gives sizeable yields. On the contrary, a variety of amino-acid esters, dipeptides, and tripeptides can be used as amino component, e.g., serine methyl ester, methionine ethyl ester, tyrosine ethyl ester, Gly–Asp

  在H 2 O溶液和含有反胶束的有机溶剂中，都研究了青霉素酰化酶催化的酰胺键的酶促合成。在酰基组分方面，反应的特异性相当高，实际上只有苯乙酸产生相当大的收率。相反，可以使用多种氨基酸酯，二肽和三肽作为氨基成分，例如丝氨酸甲酯，蛋氨酸乙酯，酪氨酸乙酯，Gly–Asp，Ala–Tyr，Gly–Tyr–Gly等等。然而，许多其他氨基酸残基不反应，并讨论了其可能的原因。产量在10％到80％之间。针对一种模型反应，提出了通过改变溶剂组成来优化收率的系统研究。该酶也能够以较低的速率偶联某些D-氨基酸残基（例如D-甲硫氨酸乙酯或Gly-D-Asp）。阳离子表面活性剂溴化十六烷基三甲基溴化铵（CTAB）在CHCl 3 /异辛烷中形成的反胶束可用于容纳青霉素酰化酶并进行酰胺合成，其中产物可能可溶于有机溶剂混合物中。研究了该反应与pH和某些胶束参数的关系，例如w o（w o = [H 2O] / [CTAB]）
• Quantitative enzymatic protection of d-amino acid methyl esters by exploiting ‘relaxed’ enantioselectivity of penicillin-G amidase in organic solvent
  作者：Chiara Carboni、Peter J.L.M. Quaedflieg、Quirinus B. Broxterman、Paolo Linda、Lucia Gardossi

  DOI：10.1016/j.tetlet.2004.10.153

  日期：2004.12

  The lower enantio selectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various D-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site. (C) 2004 Elsevier Ltd. All rights reserved.