(R)-phenylglycine benzyl ester | 68745-09-5

• 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: (R)-phenylglycine benzyl ester
• 英文别名: D-Phenylglycine-benzylester；(R)-Benzyl 2-amino-2-phenylacetate；benzyl (2R)-2-amino-2-phenylacetate
• CAS: 68745-09-5
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: VNBZYMVEHPBBJM-CQSZACIVSA-N

物化性质

• 沸点：
  362.7±27.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-phenylglycine benzyl ester 在 palladium on activated charcoal 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-N⁵-acetyl-N⁵-hydroxy-L-ornithyl-D-phenylglycine
  参考文献：
  名称：

  Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23 % yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy)carbonyl]-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g). Following alpha-amino and alpha-carboxyl deprotections of 11 and 12, EEDQ [2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline] mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36). The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5). These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

  DOI：

  10.1021/jm00107a013
• 作为产物：
  描述：

  左旋苯甘氨酸 在 三甲基氯硅烷 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 (R)-phenylglycine benzyl ester
  参考文献：
  名称：

  Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23 % yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy)carbonyl]-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g). Following alpha-amino and alpha-carboxyl deprotections of 11 and 12, EEDQ [2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline] mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36). The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5). These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

  DOI：

  10.1021/jm00107a013

文献信息

• Enantiomer recognition of organic ammonium salts by podand- and crown-type monensin amides: new synthetic strategy for chiral receptors
  作者：Kazuhiro Maruyama、Hajime Sohmiya、Hiroshi Tsukube

  DOI：10.1016/s0040-4020(01)88185-0

  日期：——

  Podand- and crown-types of new chiral receptors, characterized by a chiral polyether skeleton and an amide junction, were derived from naturally occurring monensin ionophore. Their chiral recognition ability was investigated by ion-selective electrode and 1H-NMR spectroscopic methods. Several podand-type monensin amides formed 1:1 complexes with chiral amine salts and exhibited excellent enantiomer

  具有手性聚醚骨架和酰胺键的新型手性受体的Podand和Crown类型衍生自天然莫能菌素离子载体。通过离子选择电极和1对它们的手性识别能力进行了研究1 H-NMR光谱法。几种豆荚型莫能菌素酰胺与手性胺盐形成1：1的配合物，并具有出色的对映异构体选择性。由于生物莫能菌素及其大环衍生物对手性识别的效果较差，因此假环莫能菌素腔，手性聚醚骨架和中性酰胺部分的分子组合提供了高对映异构体选择性。生物莫能菌素的化学修饰使新的离子功能显着发展，并为手性受体提供了有效的合成策略。
• Specific Inclusion of 1,2-Dimethoxybenzene Derivatives by Crystalline (<i>R</i>)-Arylglycyl-(<i>R</i>)-phenylglycines and Its Structure
  作者：Motohiro Akazome、Yukiko Yanagita、Ryo-ichi Sonobe、Katsuyuki Ogura

  DOI：10.1246/bcsj.70.2823

  日期：1997.11

  The crystallization of (R)-arylglycyl-(R)-phenylglycine (1, aryl = phenyl; 2, aryl = 1-naphthyl) in the presence of 1,2-dimethoxybenzene or its derivatives affords an inclusion compound. A single-crystal X-ray analysis has shown that, in a 1,2-dimethyoxybenzene inclusion compound, dipeptide molecules arrange in a sheet and the 1,2-dimethoxybenzene lies at the end in a void between the sheets by being

  (R)-芳基甘氨酰-(R)-苯基甘氨酸（1，芳基=苯基；2，芳基=1-萘基）在1,2-二甲氧基苯或其衍生物存在下的结晶得到包含化合物。单晶 X 射线分析表明，在 1,2-二甲氧基苯包合物中，二肽分子排列成片状，而 1,2-二甲氧基苯通过锚定在片状体之间的空隙中而位于末端片材上的氨氢通过三中心氢键。发现片材之间的距离根据客体 1,2-二甲氧基苯衍生物的长度而变化，就好像它们是支撑片材的柱子一样。
• New chiral host molecules derived from naturally occurring monensin ionophore
  作者：Kazuhiro Maruyama、Hajime Sohmiya、Hiroshi Tsukube

  DOI：10.1039/c39890000864

  日期：——

  Chemically modified monensins bearing neutral terminal groups led to effective enantiomer-selective complex formation with several amine salts in a liquid membrane-type electrode system.

  经过化学修饰的莫能菌素带有中性末端基团，可在液膜型电极系统中与几种胺盐形成有效的对映异构体选择性络合物。
• Phosphoramidate Derivatives of Guanosine Nucleoside Compunds for Treatment of Viral Infections
  申请人：Chamberlain Stanley

  公开号：US20120052046A1

  公开（公告）日：2012-03-01

  Phosphoramidate compounds derived from guanine bases having enhanced therapeutic potency are provided, and these compounds in particular have enhanced potency with respect to treatment of viral infections, such as hepatitis C virus. Pharmaceutical compositions, methods of preparing the compounds, and methods of using the compounds and compositions to treat viral infections are also provided.

  本发明提供了从鸟嘌呤碱基衍生的磷酰胺化合物，具有增强的治疗效力，特别是对于治疗病毒感染，如丙型肝炎病毒，具有增强的效力。本发明还提供了制备该化合物的制药组合物、制备该化合物的方法以及使用该化合物和组合物治疗病毒感染的方法。
• Phosphoramidate derivatives of guanosine nucleoside compounds for treatment of viral infections
  申请人：Chamberlain Stanley

  公开号：US08759318B2

  公开（公告）日：2014-06-24

  Phosphoramidate compounds derived from guanine bases having enhanced therapeutic potency are provided, and these compounds in particular have enhanced potency with respect to treatment of viral infections, such as hepatitis C virus. Pharmaceutical compositions, methods of preparing the compounds, and methods of using the compounds and compositions to treat viral infections are also provided.

  提供了从鸟嘌呤碱基衍生的磷酰胺化合物，具有增强的治疗效力，这些化合物特别具有增强的治疗病毒感染的效力，例如丙型肝炎病毒。还提供了制药组合物，制备这些化合物的方法，以及使用这些化合物和组合物治疗病毒感染的方法。