(2S)-2-[(2-羟基苯甲酰基)氨基]-3-苯基丙酸 | 56145-93-8

• 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
• 中文名称: (2S)-2-[(2-羟基苯甲酰基)氨基]-3-苯基丙酸
• 英文名称: N-(2-hydroxybenzoyl)phenylalanine
• 英文别名: N-salicyloyl-(L)-phenylalanine；N-salicyloyl-L-phenylalanine；N-salicyloylphenylalanine；salicyl phenylalanine；N-salicyloyl-L-phenylalanine；N-Salicyloyl-L-phenylalanin；L-Phenylalanine, N-(2-hydroxybenzoyl)-；(2S)-2-[(2-hydroxybenzoyl)amino]-3-phenylpropanoic acid
• CAS: 56145-93-8
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: AVPUMHMECACQJM-ZDUSSCGKSA-N

物化性质

• 沸点：
  552.6±50.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  光气 、 (2S)-2-[(2-羟基苯甲酰基)氨基]-3-苯基丙酸 在 四氢呋喃 、 三乙胺 、 甲苯 作用下， 生成 N-(N-salicyloyl-DL-phenylalanyl)-glycine methyl ester
  参考文献：
  名称：

  Gemischte Anhydrideabocarboxyy-AminosäurenundChlorameisensäurezur Veresterung von aromatischen和aliphatischen羟基-Verbindungen

  摘要：

  N-Cbzo-α-Aminosäure-Restes在醇和酚醛中的反应 死于“艾诺尔·里贝·冯·贝斯皮伦·贝希里本”的“光致发光二极管”。

  DOI：

  10.1002/hlca.19570400315
• 作为产物：
  描述：

  邻乙酰水杨酰氯 在 palladium hydroxide - carbon 、 氢气 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 16.0h， 生成 (2S)-2-[(2-羟基苯甲酰基)氨基]-3-苯基丙酸
  参考文献：
  名称：

  Convenient Preparation ofN-Salicyloyl-(L)-phenylalanine

  摘要：

  N-salicyloyl-(L)-phenylalanine was prepared by a simple, two-step process from (L)-phenylalanine benzyl ester and acetylsalicyloyl chloride followed by hydrolysis and catalytic hydrogenation in an overall yield of 85%.

  DOI：

  10.1080/00397919608003627

文献信息

• Desferrioxamine oral delivery system
  申请人：Emisphere Technologies, Inc.

  公开号：EP1072255A2

  公开（公告）日：2001-01-31

  Modified amino acids and methods for their preparation and use as oral delivery systems for pharmaceutical agents are described. The modified amino acids are preparable by reacting single amino acids or mixtures of two or more kinds of amino acids with an amino modifying agent such as benzene sulfonyl chloride, benzoyl chloride, and hippuryl chloride. The modified amino acids may form encapsulating microspheres in the presence of the active agent under sphere-forming conditions. Alternatively, the modified amino acids may be used as a carrier by simply mixing the amino acids with the active agent. The preferred acylated amino acid carrier is salicyloyl-phenylalanine. The modified amino acids are particularly useful in delivering biologically active agents, e.g., desferrioxamine, insulin or cromolyn sodium, or other agents which are sensitive to the denaturing conditions of the gastrointestinal tract.

  本文介绍了改性氨基酸及其制备方法和用作药物口服给药系统的方法。改性氨基酸的制备方法是将单一氨基酸或两种或两种以上氨基酸的混合物与氨基改性剂（如苯磺酰氯、苯甲酰氯和海波瑞酰氯）反应。在成球条件下，改性氨基酸可在活性剂存在下形成包封微球。另外，改性氨基酸也可用作载体，只需将氨基酸与活性剂混合即可。首选的酰化氨基酸载体是水杨酰苯丙氨酸。改性氨基酸特别适用于输送生物活性制剂，例如去铁胺、胰岛素或色甘酸钠，或其他对胃肠道变性条件敏感的制剂。
• Methods and compositions for inducing oral tolerance in mammals
  申请人：——

  公开号：US20020061311A1

  公开（公告）日：2002-05-23

  The present invention relates to methods and pharmaceutical formulations for orally delivering an antigen to induce tolerance. The antigen is combined with derivatized amino acids or salts thereof. The induction of oral tolerance may be applied clinically for the prevention or treatment of auto-immune diseases and clinical allergic hypersensitivities, and for the prevention of allograft rejection.

  本发明涉及口服递送抗原以诱导耐受的方法和药物制剂。抗原与衍生氨基酸或其盐结合。诱导口服耐受性可应用于临床，预防或治疗自身免疫性疾病和临床过敏性超敏反应，以及预防同种异体移植排斥反应。
• A Kinetic Study into the Hydrolysis of the Ochratoxins and Analogues by Carboxypeptidase A
  作者：Maria A. Stander、Pieter S. Steyn、Francois H. van der Westhuizen、Barry E. Payne

  DOI：10.1021/tx000221i

  日期：2001.3.1

  The hydrolyses of the ochratoxins and analogues by carboxypeptidase A were assessed. This was done by measuring the amount of phenylalanine formed with liquid chromatography coupled to tandem electrospray mass spectrometry. The kinetic data of ochratoxin A, ochratoxin B, and the synthetic bromo-ochratoxin B were compared to the values of a number of synthesized structure analogues, namely, ochratoxin A methyl ester, ochratoxin B methyl ester, N-(2-hydroxybenzoyl)phenylalanine, N-(5-chloro-2-hydroxybenzoyl)phenylalanine, N-(5-bromo-2-hydroxybenzoyl)phenylalanine, and N-(5-fluoro-2-hydroxybenzoyl)phenylalanine, and N-(5-fluoro-2-hydroxybenzoyl)phenylalanine, The halogen-containing analogues had lower turnovers than their des-halo analogues. There are no substantial differences in the kinetic data between the different halogen-containing analogues.
• Microsphere Formation in a Series of Derivatized .alpha.-Amino Acids: Properties, Molecular Modeling, and Oral Delivery of Salmon Calcitonin
  作者：Andrea Leone-Bay、Campbell McInnes、NaiFang Wang、Frenel DeMorin、Doug Achan、Christine Lercara、Donald Sarubbi、Susan Haas、Jeffery Press

  DOI：10.1021/jm00021a014

  日期：1995.10

  A series of benzoylated and phenylsulfonylated amino acids are novel, low molecular weight, self-assembling molecules. At low pH, these compounds form microspheres that dissolve readily under neutral conditions. In a given synthetic series, those molecules with low aqueous solubility formed microspheres more readily than did the molecules possessing high water solubility, suggesting that the hydrophobicity of these compounds contributes to the ability to form microspheres. In addition, molecular modeling studies on selected compounds have shown that microsphere formation may depend also on various aromatic ring and dipole-dipole interactions, which could effect the extent and types of favorable stacking conformations between molecules. The microspheres prepared from these compounds have been used to effect the oral delivery of salmon calcitonin, a model protein drug, in both rodents and primates.
• Steyn, Pieter S.; Payne, Barry E., South African Journal of Chemistry, 1999, vol. 52, # 2-3, p. 69 - 70
  作者：Steyn, Pieter S.、Payne, Barry E.

  DOI：——

  日期：——