甲基N-[(苄氧基)羰基]-L-beta-天冬氨酰-L-苯丙氨酸酯 | 35739-01-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 中文名称: 甲基N-[(苄氧基)羰基]-L-beta-天冬氨酰-L-苯丙氨酸酯
• 英文名称: 1-Methyl 3-phenyl-N-(N-((phenylmethoxy)carbonyl)-L-beta-aspartyl)-L-alaninate
• 英文别名: (2S)-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 35739-01-6
• 化学式: C₂₂H₂₄N₂O₇
• 分子量: 428.442
• InChiKey: CLVVEIINFJLFNK-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基N-[(苄氧基)羰基]-L-beta-天冬氨酰-L-苯丙氨酸酯 、 甲酸 生成 β-asp-phe甲基酯
  参考文献：
  名称：

  BAUM, LASZLO;SZABO, SUZANNE;BLANC, GERALD

  摘要：

  DOI：
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 N-Benzyloxycarbonyl-DL-asparaginsaeure-anhydrid 生成 甲基N-[(苄氧基)羰基]-L-beta-天冬氨酰-L-苯丙氨酸酯
  参考文献：
  名称：

  AURICCHIO, S.;MINISCI, F.

  摘要：

  DOI：

文献信息

• 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。
• Preparation of n-protected alpha-l-aspartyl-l-phenylalanine methyl ester
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0334236A2

  公开（公告）日：1989-09-27

  Disclosed are a process for preparing N-protected aspartic anhydride by the reaction of N-protected aspartic acid with phosgene, a process for preparing an N-protected α-L-aspartyl-L-phenylalanine methyl ester from N-protected aspartic anhydride and mineral acid salt of L-phenylalanine methyl ester, and a process for preparing N-benzyloxy­carbonyl-L-aspartic anhydride by the reaction of N-­benzyloxycarbonyl-L-aspartic acid with acetic anhydride.

  本发明公开了一种通过 N-保护天冬氨酸与光气反应制备 N-保护天冬氨酸酐的工艺、一种通过 N-保护天冬氨酸和 L-苯丙氨酸甲酯的矿物酸盐制备 N-保护α-L-天冬氨酰-L-苯丙氨酸甲酯的工艺、以及一种通过 N-苄氧羰基-L-天冬氨酸与乙酸酐反应制备 N-苄氧羰基-L-天冬氨酸酐的工艺、以及一种通过 N-苄氧羰基-L-天冬氨酸与乙酸酐反应制备 N-苄氧羰基-L-天冬氨酸酐的工艺。
• Separation method of alpha-L-aspartyl-L-phenylalanine methyl ester
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0333036A2

  公开（公告）日：1989-09-20

  A method for separating α-L-aspartyl-L-­phenylalanine methyl ester (α-APM) from a solution containing α-APM and impurities associated with the production thereof which comprises adding a mineral acid or an organic sulfonic acid to the solution in an organic carboxylic acid or in a solvent containing an organic carboxylic acid, and isolating the pure salt of α-APM which precipitates therefrom.

  一种从含有α-APM和与生产α-APM有关的杂质的溶液中分离α-L-天冬氨酰-L-苯丙氨酸甲酯（α-APM）的方法，该方法包括向有机羧酸或含有有机羧酸的溶剂中的溶液中加入一种矿物酸或一种有机磺酸，并分离出从中析出的α-APM纯盐。
• Preparation process of alpha-aspartyl-L-phenylalanine methyl ester
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0510552A1

  公开（公告）日：1992-10-28

  α-L-Aspartyl-L-phenylalanine methyl ester (α-APM) is prepared by catalytic hydrogenation of N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester (Z-α-APM). The catalytic hydrogenation is conducted in an aqueous suspension containing the Z-α-APM in the form of particles whose average particle size is not greater than 800 µm. The starting Z-α-APM may contain up to 30 wt.% of its β-isomer provided that the process additionally includes recrystallization of the α-APM, collection of the α-APM by filtration and recycling of the filtrate for use in the aqueous suspension of Z-α-APM.

  α-L-天冬氨酰-L-苯丙氨酸甲酯（α-APM）是通过催化加氢 N-苄氧羰基-α-L-天冬氨酰-L-苯丙氨酸甲酯（Z-α-APM）制备的。催化氢化在含有 Z-α-APM 的水悬浮液中进行，Z-α-APM 为平均粒径不大于 800 微米的颗粒形式。起始 Z-α-APM 可含有多达 30 重量％的其 β-异构体，条件是该工艺还包括 α-APM 的重结晶、通过过滤收集 α-APM 以及回收滤液用于 Z-α-APM 的水悬浮液。
• Effects of solvents and additives on the reaction of N-(benzyloxycarbonyl)-L-aspartic anhydride with L-phenylalanine methyl ester (synthesis of aspartame)
  作者：Chin Ping Yang、Chein Shyong Su

  DOI：10.1021/jo00376a025

  日期：1986.12