(1S,3R,1'S) 3-(benzoylamino-ethoxycarbonylmethyl)cyclopentanecarboxylic acid | 878560-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,3R,1'S) 3-(benzoylamino-ethoxycarbonylmethyl)cyclopentanecarboxylic acid
• 英文别名: (1S,3R,1'S)-3-(1'-(benzoylamino)-1'-carboxymethyl)cyclopentanecarboxylic acid；(1S,3R)-3-[(S)-benzamido(carboxy)methyl]cyclopentane-1-carboxylic acid
• CAS: 878560-10-2
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: VTLXGUULVVHUHD-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3R,1'S) 3-(benzoylamino-ethoxycarbonylmethyl)cyclopentanecarboxylic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 生成 (1S,3R)-3-[(S)-amino(carboxy)methyl]cyclopentane-1-carboxylic acid
  参考文献：
  名称：

  Synthetic peptides containing a conserved sequence motif of the Id protein family modulate vascular smooth muscle cell phenotype

  摘要：

  Modulation of smooth muscle cells to a proliferating and migrating phenotype with downregulated alpha-actin expression is observed upon vascular lesion formation. The Id proteins (inhibitors of cell differentiation) play a role in the development of this phenotype. In contrast, synthetic peptides based on a conserved 11-residue Id sequence trigger the switch to a contractile phenotype that shows reduced cell growth and migration, increased expression of alpha-actin and decreased Id protein levels. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.105
• 作为产物：
  描述：

  (-)-8-phenylmenthyl (Z)-2-(benzoylamino)-3-hydroxyacrylate 在 palladium on activated charcoal 吡啶 、 lithium hydroxide 、 magnesium(II) perchlorate 、 水 、 氢气 、 sodium carbonate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， -10.0~25.0 ℃ 、101.33 kPa 条件下， 反应 94.5h， 生成 (1S,3R,1'S) 3-(benzoylamino-ethoxycarbonylmethyl)cyclopentanecarboxylic acid
  参考文献：
  名称：

  Enantioselective synthesis of epimeric cis-3-carboxycyclopentylglycines

  摘要：

  Two epimeric chiral cyclopentylglycines (-)-16 and (+)-17, functionalised with a carboxy group cis to the amino acid group, were prepared starting from chiral 2-amino-3-oxo-norbornanecarboxylic acid derivative exo-9 by combining two classical reactions such as the Diels-Alder and retro-Claisen reactions. Compounds 16 and 17 are non-proteinogenic amino acids of biological interest containing conformational constraints in which the skeletons of both 2-aminoadipic acid and 2-aminopimelic acid are included. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.011

文献信息

• Chemoenzymatic resolution of epimeric cis 3-carboxycyclopentylglycine derivatives
  作者：Chiara Cabrele、Francesca Clerici、Raffaella Gandolfi、Maria Luisa Gelmi、Francesco Molinari、Sara Pellegrino

  DOI：10.1016/j.tet.2006.02.006

  日期：2006.4

  reactions. The synthesis incorporates a concise and inexpensive chemoenzymatic resolution of racemic compounds 4,5a, the N,O-protected derivatives of amino acids 10,11. Systematic screening with different enzymes and microorganisms was performed to select a very efficient catalyst for the separation of the racemic mixtures. The reaction conditions allowing deprotection of both ester and amino functions

  通过一系列Diels-Alder反应和Retro-Claisen反应，有效地制备了差向异构的3-羧基环戊基甘氨酸（+）- 10 /（-）- 10和（+）- 11 /（-）- 11。合成结合了简明和外消旋化合物的廉价的化学酶促分辨率4，图5a，所述Ñ，Ó氨基酸-保护的衍生物10，11。用不同的酶和微生物进行系统筛选以选择一种非常有效的催化剂，用于分离外消旋混合物。研究了允许脱保护酯和氨基官能团并避免差向异构化过程的反应条件。以高对映体纯度获得对映体（即，（+）- 10 /（-）- 10和（+）- 11 /（-）- 11）。明确分配了所有立体中心的绝对配置。
• Enantioselective synthesis of epimeric cis-3-carboxycyclopentylglycines
  作者：Francesco Caputo、Francesca Clerici、Maria Luisa Gelmi、Sara Pellegrino、Tullio Pilati

  DOI：10.1016/j.tetasy.2005.11.011

  日期：2006.1

  Two epimeric chiral cyclopentylglycines (-)-16 and (+)-17, functionalised with a carboxy group cis to the amino acid group, were prepared starting from chiral 2-amino-3-oxo-norbornanecarboxylic acid derivative exo-9 by combining two classical reactions such as the Diels-Alder and retro-Claisen reactions. Compounds 16 and 17 are non-proteinogenic amino acids of biological interest containing conformational constraints in which the skeletons of both 2-aminoadipic acid and 2-aminopimelic acid are included. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthetic peptides containing a conserved sequence motif of the Id protein family modulate vascular smooth muscle cell phenotype
  作者：Sara Pellegrino、Nicola Ferri、Noemi Colombo、Edoardo Cremona、Alberto Corsini、Roberto Fanelli、Maria Luisa Gelmi、Chiara Cabrele

  DOI：10.1016/j.bmcl.2009.09.105

  日期：2009.11

  Modulation of smooth muscle cells to a proliferating and migrating phenotype with downregulated alpha-actin expression is observed upon vascular lesion formation. The Id proteins (inhibitors of cell differentiation) play a role in the development of this phenotype. In contrast, synthetic peptides based on a conserved 11-residue Id sequence trigger the switch to a contractile phenotype that shows reduced cell growth and migration, increased expression of alpha-actin and decreased Id protein levels. (C) 2009 Elsevier Ltd. All rights reserved.