Z-L.-Phe-Glc | 109345-32-6

• 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: Z-L.-Phe-Glc
• 英文别名: 1-O-(N-cbz-l-phenylalanyl)glycerol；2,3-dihydroxypropyl (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 109345-32-6
• 化学式: C₂₀H₂₃NO₆
• 分子量: 373.406
• InChiKey: FEZGGARFTLTKOS-ZVAWYAOSSA-N

物化性质

• 沸点：
  598.6±50.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-L.-Phe-Glc 在 palladium/alumina Novozyme 、 3-戊酮 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  化学酶促合成氨基酸基表面活性剂

  摘要：

  AbstractThe application of lipases to the synthesis of amino acid‐based surfactants was investigated. Low yields (2–9%) were obtained in the acylation of free amino acids, such as l‐serine and l‐lysine, as well as their ethyl esters and amides with fatty acids, owing in part to low miscibility of the reactants. When the N‐carbobenzyloxy (Cbz)‐l‐amino acids were used in an effort to improve miscibility of the amino acid derivatives with the acyl donor, a dramatic improvement was observed for N‐Cbz‐l‐serine (92% yield) but not for Nα‐Cbz‐ or Nζ‐Cbz‐l‐lysine (7 and 2% yield, respectively). As an alternative, and efficient synthesis of Nζ‐acyl‐l‐lysines was developed, based on the regiospecific chemical acylation of copper(II) lysinate. In pursuit of a general route to amino acid‐fatty acid surfactants, the utility of a polyol linker was investigated. Thus, the glycerol ester of Nα′Nζ‐di‐Cbz‐l‐lysine was prepared and evaluated as a substrate for acylation. As expected, this and other glycer‐1‐yl esters of N‐protected amino acids were excellent substrates for lipase‐catalyzed acylation. Their reaction with myristic acid in the presence of Novozyme resulted in the regioselective acylation of the primary hydroxyl group of the glycerol moiety to afford the corresponding 1‐O‐(N‐Cbz‐l‐aminoacyl)‐3‐O‐myris‐toylglycerols with conversions of 50–90%. These were readily deprotected to give a range of 1‐O‐(aminoacyl)‐3‐O‐myristoyl‐glycerols with overall yields of 27–71%.

  DOI：

  10.1007/s11746-997-0232-8
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 、 甘油 在 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Z-L.-Phe-Glc
  参考文献：
  名称：

  化学酶促合成氨基酸基表面活性剂

  摘要：

  AbstractThe application of lipases to the synthesis of amino acid‐based surfactants was investigated. Low yields (2–9%) were obtained in the acylation of free amino acids, such as l‐serine and l‐lysine, as well as their ethyl esters and amides with fatty acids, owing in part to low miscibility of the reactants. When the N‐carbobenzyloxy (Cbz)‐l‐amino acids were used in an effort to improve miscibility of the amino acid derivatives with the acyl donor, a dramatic improvement was observed for N‐Cbz‐l‐serine (92% yield) but not for Nα‐Cbz‐ or Nζ‐Cbz‐l‐lysine (7 and 2% yield, respectively). As an alternative, and efficient synthesis of Nζ‐acyl‐l‐lysines was developed, based on the regiospecific chemical acylation of copper(II) lysinate. In pursuit of a general route to amino acid‐fatty acid surfactants, the utility of a polyol linker was investigated. Thus, the glycerol ester of Nα′Nζ‐di‐Cbz‐l‐lysine was prepared and evaluated as a substrate for acylation. As expected, this and other glycer‐1‐yl esters of N‐protected amino acids were excellent substrates for lipase‐catalyzed acylation. Their reaction with myristic acid in the presence of Novozyme resulted in the regioselective acylation of the primary hydroxyl group of the glycerol moiety to afford the corresponding 1‐O‐(N‐Cbz‐l‐aminoacyl)‐3‐O‐myris‐toylglycerols with conversions of 50–90%. These were readily deprotected to give a range of 1‐O‐(aminoacyl)‐3‐O‐myristoyl‐glycerols with overall yields of 27–71%.

  DOI：

  10.1007/s11746-997-0232-8

文献信息

• Use of nonproteases in peptide synthesis
  作者：J.Blair West、Chi-Huey Wong

  DOI：10.1016/s0040-4039(00)95377-2

  日期：1987.1
• Chemo-enzymatic synthesis of amino acid-based surfactants
  作者：Rao Valivety、Paula Jauregi、Iqbal Gill、Evgeny Vulfson

  DOI：10.1007/s11746-997-0232-8

  日期：1997.7

  AbstractThe application of lipases to the synthesis of amino acid‐based surfactants was investigated. Low yields (2–9%) were obtained in the acylation of free amino acids, such as l‐serine and l‐lysine, as well as their ethyl esters and amides with fatty acids, owing in part to low miscibility of the reactants. When the N‐carbobenzyloxy (Cbz)‐l‐amino acids were used in an effort to improve miscibility of the amino acid derivatives with the acyl donor, a dramatic improvement was observed for N‐Cbz‐l‐serine (92% yield) but not for Nα‐Cbz‐ or Nζ‐Cbz‐l‐lysine (7 and 2% yield, respectively). As an alternative, and efficient synthesis of Nζ‐acyl‐l‐lysines was developed, based on the regiospecific chemical acylation of copper(II) lysinate. In pursuit of a general route to amino acid‐fatty acid surfactants, the utility of a polyol linker was investigated. Thus, the glycerol ester of Nα′Nζ‐di‐Cbz‐l‐lysine was prepared and evaluated as a substrate for acylation. As expected, this and other glycer‐1‐yl esters of N‐protected amino acids were excellent substrates for lipase‐catalyzed acylation. Their reaction with myristic acid in the presence of Novozyme resulted in the regioselective acylation of the primary hydroxyl group of the glycerol moiety to afford the corresponding 1‐O‐(N‐Cbz‐l‐aminoacyl)‐3‐O‐myris‐toylglycerols with conversions of 50–90%. These were readily deprotected to give a range of 1‐O‐(aminoacyl)‐3‐O‐myristoyl‐glycerols with overall yields of 27–71%.