N-benzyloxycarbonyl-L-aspartic anhydride | 88966-25-0

• 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-benzyloxycarbonyl-L-aspartic anhydride
• 英文别名: N-carbobenzyloxy-L-aspartic anhydride；N-carbobenzoxy-L-aspartic anhydride；(3S)-4-[(2S)-3-carboxy-2-(phenylmethoxycarbonylamino)propanoyl]oxy-4-oxo-3-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 88966-25-0
• 化学式: C₂₄H₂₄N₂O₁₁
• 分子量: 516.461
• InChiKey: BOFFAQPRQXZJGV-ROUUACIJSA-N

物化性质

• 沸点：
  772.7±60.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-L-aspartic anhydride 在 硫酸 、 二环己胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 N-[苄氧羰基]-L-天冬氨酸 4-叔丁酯 1-甲酯
  参考文献：
  名称：

  Scoffone,E. et al., Gazzetta Chimica Italiana, 1964, vol. 94, p. 695 - 709

  摘要：

  DOI：
• 作为产物：
  描述：

  N-CBZ-L-天冬氨酸 以 正己烷 、 乙酸酐 为溶剂， 生成 N-benzyloxycarbonyl-L-aspartic anhydride
  参考文献：
  名称：

  Naphthyridine antianaerobic compounds

  摘要：

  公开号：

  EP0302372B1

文献信息

• [EN] CYCLOPENTYL GLUTARAMIDES AND THEIR USE AS NEUTRAL ENDOPEPTIDASE INHIBITORS<br/>[FR] GLUTARAMIDES CYCLOPENTYLE ET UTILISATION DE CES COMPOSES COMME INHIBITEURS D'ENDOPEPTIDASE NEUTRE (NEP)
  申请人：PFIZER LTD

  公开号：WO2004056787A1

  公开（公告）日：2004-07-08

  The invention relates to NEP inhibitors for treating cardiovascular disorders wherein R1 is C1-C6alkyl, C1-C6alkoxyC1-C3alkyl or C1-C6alkoxyC1-C6alkoxyC,-C3alkyl; R2 is hydrogen or C1-C6alkyl; L is an aromatic heterocyclic ring, optionally substituted with C,­ C6alkyl or halo; R3 is C1-C6alkyl optionally substituted by halo, alkoxy, haloalkoxy, alkylthio, haloalkylthio or nitrile group, or R3 is phenyl or aromatic heterocyclyl each of which may be independently substituted by one or more alkyl, halo, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or nitrile group; R4 and R5 are either both hydrogen, or one of R4 and R5 is hydrogen and the other is a biolabile ester-forming group that in the body of a patient is replaced by hydrogen; p is 0, 1 or 2; and q is 1 or 2.

  该发明涉及NEP抑制剂，用于治疗心血管疾病，其中R1为C1-C6烷基，C1-C6烷氧基C1-C3烷基或C1-C6烷氧基C1-C6烷氧基，R2为氢或C1-C6烷基，L为芳香杂环环，可选择性地取代为C，C6烷基或卤素，R3为C1-C6烷基，可选择性地取代为卤素，烷氧基，卤代烷氧基，烷基硫醚，卤代烷基硫醚或腈基，或R3为苯基或芳香杂环基，每个基团可独立地取代为一个或多个烷基，卤素，卤代烷基，烷氧基，卤代烷氧基，烷基硫醚，卤代烷基硫醚或腈基；R4和R5要么都是氢，要么R4和R5中的一个是氢，另一个是在患者体内被氢取代的生物易降解酯基团；p为0、1或2；q为1或2。
• Molecularly Imprinted Polymeric Adsorbents for Byproduct Removal
  作者：Lei Ye、Olof Ramström、Klaus Mosbach

  DOI：10.1021/ac980069d

  日期：1998.7.1

  In this study, both diastereo- and enantioselective adsorbents for a dipeptide derivative were prepared using a molecular imprinting technique. The diastereo- and enantioisomers for the dipeptide derivative N-(benzyloxycarbonyl)aspartylphenylalanine methyl ester (ZAPM), in addition to the α- and β-isomers, were chosen as test compounds for the investigation of the imprinting effect. The close similarities between the structures of different isomers make it possible to interpret the roles of template structure on specific molecular recognition. A highly specific byproduct scavenger was prepared by simultaneously incorporating methacrylic acid and vinylpyridine as functional monomers. The binding selectivities of polymeric adsorbents for the α- and β-isomers are shown to be greatly enhanced by introducing enantiocomplementarities into the polymer matrixes. An anti-β-l,l-ZAPM polymer was applied in a solid-phase extraction protocol, for the purification of the product in the chemical synthesis of N-protected aspartame. Finally, polymer beads were also imprinted against β-l,l-ZAPM using suspension polymerization performed in perfluorocarbon fluid. The imprinted polymer beads displayed the same binding characteristics as the imprinted bulk polymer and can be envisaged for the use of product purification in chromatographic mode.

  本研究采用分子印迹技术制备了一种二肽衍生物的非对映和对映选择性吸附剂。二肽衍生物 N-(苄氧羰基)天冬苯丙氨酸甲酯（ZAPM）的非对映异构体和对映异构体，以及α-和β-异构体被选为研究印迹效应的测试化合物。不同异构体结构之间的相似性使得解释模板结构对特定分子识别的作用成为可能。通过同时加入甲基丙烯酸和乙烯基吡啶作为功能单体，制备出了一种高特异性副产物清除剂。通过在聚合物基质中引入对映体互补性，聚合物吸附剂对 α 和 β 异构体的结合选择性大大提高。一种抗β-l,l-ZAPM 聚合物被应用于固相萃取方案，用于纯化 N 保护天冬酰胺化学合成中的产物。最后，还利用在全氟碳化物流体中进行的悬浮聚合法，对 β-l,l-ZAPM聚合物进行了压印。压印聚合物珠显示出与压印块状聚合物相同的结合特性，可用于色谱模式下的产品纯化。
• [EN] NEUTRAL ENDOPEPTIDASE INHIBITOR POLYMORPH<br/>[FR] POLYMORPHE INHIBITEUR D'ENDOPEPTIDASE NEUTRE
  申请人：PFIZER LTD

  公开号：WO2005123702A1

  公开（公告）日：2005-12-29

  Disclosed are (2S)-2-1-[(1S)-1-Isobutoxycarbonyl-2-(5-phenyl-oxazol-2-yl)-ethylcarbamoyl]-cyclopentylmethyl}-4-methoxy-butyric, Potassium-(2S)-2-1-[(1S)-1-Isobutoxycarbonyl-2-(5-phenyl-oxazol-2-yl)-ethylcarbamoyl]-cyclopentylmethyl}-4-methoxy-butyrate, monohydrate and its Form I polymorph. Also disclosed are compositions of the described forms, kits including the described forms, and methods of using the described forms for the treatment diseases or disorders where the use of a neutral endopeptidase inhibitor is indicated, including cardiovascular diseases and conditions.

  披露了(2S)-2-1-[(1S)-1-异丁氧羰基-2-(5-苯基-噁唑-2-基)-乙基氨基]-环戊甲基}-4-甲氧基丁酸钾盐、(2S)-2-1-[(1S)-1-异丁氧羰基-2-(5-苯基-噁唑-2-基)-乙基氨基]-环戊甲基}-4-甲氧基丁酸盐、单水合物及其I型多形体。还披露了所述形式的组合物、包含所述形式的试剂盒，以及使用所述形式治疗心血管疾病和症状等需要使用中性内肽酶抑制剂的疾病或疾病的方法。
• [EN] SELF-ASSEMBLING PEPTIDE AMPHIPHILES AND RELATED METHODS FOR GROWTH FACTOR DELIVERY<br/>[FR] AMPHIPHILES PEPTIDIQUES A ASSEMBLAGE AUTOMATIQUE ET PROCEDES ASSOCIES D'ADMINISTRATION DE FACTEUR DE CROISSANCE
  申请人：UNIV NORTHWESTERN

  公开号：WO2005056039A1

  公开（公告）日：2005-06-23

  Amphiphilic peptide compounds comprising one or more epitope sequences for binding interaction with one or more corresponding growth factors, micellar assemblies of such compounds and related methods of use.

  含有一种或多种表位序列的两亲性肽化合物，用于与一种或多种相应生长因子的结合相互作用，这些化合物的胶束组装体及其相关使用方法。
• Process for producing 1H-3-aminopyrrolidine and derivatives thereof
  申请人：Mitsubishi Chemical Corporation

  公开号：US20020042523A1

  公开（公告）日：2002-04-11

  A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R′NH 2 , subjecting the reaction product to cyclodehydration to obtain an optically active 1 -aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.

  公开了一种生产1H-3-氨基吡咯烷及其衍生物的方法。该方法特别适用于生产光学活性的1H-3-氨基吡咯烷及其衍生物，其中包括将公式（1）表示的光学活性氨基保护的天冬氨酸酐与公式R'NH2表示的一级胺反应，将反应产物经过环化脱水作用得到公式（2）表示的光学活性1-芳基甲基-3-(保护氨基)吡咯烷-2,5-二酮化合物，随后消除公式（2）所表示的化合物中3位氨基基团的保护基，得到公式（3）表示的光学活性1-芳基甲基-3-氨基吡咯烷-2,5-二酮化合物，将公式（3）所表示的化合物的羰基基团还原，得到公式（4）表示的光学活性1-芳基甲基-3-氨基吡咯烷化合物或其与质子酸的盐，然后将公式（4）所表示的化合物或其盐进行氢解，得到光学活性的1H-3-氨基吡咯烷或其质子酸盐。