H-β-Asp-Phe-OH | 13433-10-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: H-β-Asp-Phe-OH
• 英文别名: Asp-β-Phe；beta-Aspartylphenylalanine；(2S)-2-amino-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobutanoic acid
• CAS: 13433-10-8
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: KDGAYJIGGCDHPH-UWVGGRQHSA-N

物化性质

• 沸点：
  606.9±55.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  3-苯基-L-丙氨酸苄酯 在 钯 氢气 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 H-β-Asp-Phe-OH
  参考文献：
  名称：

  一些二肽的结构-味道关系。

  摘要：

  DOI：

  10.1021/ja01038a046

文献信息

• BETA-HAIRPIN PEPTIDOMIMETICS AS SELECTIVE ELASTASE INHIBITORS
  申请人：POLYPHOR AG

  公开号：US20160333053A1

  公开（公告）日：2016-11-17

  β-Hairpin peptidomimetics of the general formula cyclo(-Xaa 1 -Xaa 2 -Thr 3 -Xaa 4 -Ser 5 -Xaa 6 -Xaa 7 -Xaa 8 -Xaa 9 -Xaa 10 -Xaa 11 -Xaa 12 -Xaa 13 -) and pharmaceutically acceptable salts thereof, with Xaa 1 , Xaa 2 , Xaa 4 , Xaa 6 , Xaa 7 , Xaa 8 , Xaa 9 , Xaa 10 , Xaa 11 , Xaa 12 and Xaa 13 being amino acid residues of certain types which are defined in the description and the claims, have elastase inhibitory properties, especially against human neutrophil elastase, and can be used for preventing infections or diseases related to such infections in healthy individuals or for slowing infections in infected patients. The compounds of the invention can further be used where cancer, or immunological diseases, or pulmonary diseases, or cardiovascular diseases, or neurodegenerative diseases, or inflammation, or diseases related to inflammation, are mediated or resulting from elastase activity. These peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  β-头发环肽类似物的一般公式为cyclo(-Xaa1-Xaa2-Thr3-Xaa4-Ser5-Xaa6-Xaa7-Xaa8-Xaa9-Xaa10-Xaa11-Xaa12-Xaa13-)及其药学上可接受的盐，其中Xaa1、Xaa2、Xaa4、Xaa6、Xaa7、Xaa8、Xaa9、Xaa10、Xaa11、Xaa12和Xaa13是在描述和权利要求中定义的某些类型的氨基酸残基，具有弹性酶抑制性质，特别是对人类中性粒细胞弹性蛋白酶，可用于预防健康个体中与此类感染相关的感染或疾病，或者用于减缓感染患者中的感染。该发明的化合物还可用于癌症、免疫性疾病、肺部疾病、心血管疾病、神经退行性疾病、炎症或与炎症相关的疾病由弹性酶活性介导或由此导致的情况。这些肽类似物可以通过基于混合固相和溶液相合成策略的过程制造。
• Method for reductive elimination of protecting groups and preparative process using such method
  申请人：AJINOMOTO CO., INC.

  公开号：EP0027319A2

  公开（公告）日：1981-04-22

  The invention provides a novel and efficient method for the elimination of protecting groups, e.g. benzyloxycarbonyl group, from a protected amino acid, peptide or derivative thereof having at least one functional group protected by a protecting group, e.g. a lower alkyl ester of N-benzyloxycarbonyl-a- L-aspartyl-L-phenylalanine by catalytic hydrogen reduction to produce free amino acid, peptide or derivative thereof. In contrast to the conventional procedures in which the reaction is carried out in a solvent dissolving both the starting compound and the product compound or a solvent dissolving the starting compound but not dissolving the product compound, the inventive method utilizes a binary two-phase reaction medium composed of water and an organic solvent not freely miscible with water such as toluene. The reaction takes place in the organic phase containing the starting compound dissolved and the catalyst dispersed therein whereas the reaction product which is watersoluble is smoothly and successively transferred into the aqueous phase so that advantages are obtained in the unexpectedly high yield of the product as well as in the easiness of handling the reaction mixture after completion of the reaction.

  本发明提供了一种新颖有效的方法，通过催化氢还原法从至少有一个官能团受保护基（如N-苄氧羰基-a-L-天冬氨酰-L-苯丙氨酸的低级烷基酯）保护的氨基酸、肽或其衍生物中消除保护基（如苄氧羰基），生成游离氨基酸、肽或其衍生物。与在同时溶解起始化合物和产物化合物的溶剂中进行反应或在溶解起始化合物但不溶解产物化合物的溶剂中进行反应的传统程序不同，本发明的方法利用由水和不能与水自由混溶的有机溶剂（如甲苯）组成的二元两相反应介质。反应在有机相中进行，有机相中含有溶解的起始化合物和分散在其中的催化剂，而水溶性反应产物则被顺利地连续转移到水相中，这样就获得了出乎意料的高产率以及反应完成后易于处理反应混合物的优点。
• Process for the preparation of alpha-L-aspartyl-L-phenylalanine methyl ester
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0187530A2

  公开（公告）日：1986-07-16

  Process for preparing α-L-aspartyl-L-phenylalanine methyl ester which comprises treating, as a raw material, N-formyl-a-L-aspartyl-L-phenylalanine in methanol in the presence of an acid to form a-L-aspartyl-L-phenylalanine dimethyl ester, hydrolyzing the α-L-aspartyl-L-phenylalanine dimethyl ester by bringing it into contact with hydrochloric acid in the presence of methanol as desired, separating the thereby-precipitated a-L-aspartyl-L-phenylalanine methyl ester hydrochloride and neutralizing the hydrochloride. The raw material may contain N-formyl-β-L-aspartyl-L-phenylalanine in an amount of 30% by weight or less.

  制备α-L-天冬氨酰-L-苯丙氨酸甲酯的工艺，包括将 N-甲酰基-a-L-天冬氨酰-L-苯丙氨酸作为原料，在甲醇中并在酸的存在下进行处理，形成 a-L-天冬氨酰-L-苯丙氨酸二甲酯；根据需要，在甲醇的存在下，通过使α-L-天冬氨酰-L-苯丙氨酸二甲酯与盐酸接触，水解该α-L-天冬氨酰-L-苯丙氨酸二甲酯；分离由此沉淀的 a-L-天冬氨酰-L-苯丙氨酸甲酯盐酸盐，并中和该盐酸盐。 原料中 N-甲酰基-β-L-天冬氨酰-L-苯丙氨酸的含量可为 30%（按重量计）或更少。
• Process for separation of N-protected alpha-L-aspartyl-L-phenylalanines
  申请人：Ajinomoto Co., Inc.

  公开号：EP0256812A2

  公开（公告）日：1988-02-24

  Disclosed herein is a process for separating N-­protected-α-L-aspartyl-L-phenylalanine, more particularly a process for selectively separating N-protected-α-L-aspartyl-­L-phenylalanine from a solution of N-protected-α-L-aspartyl-­L-phenylalanine containing at least N-protected-α-L-aspartyl-­D-phenylalanine as impurity.

  本文公开了一种分离 N-保护-α-L-天冬氨酰-L-苯丙氨酸的工艺，特别是从至少含有 N-保护-α-L-天冬氨酰-D-苯丙氨酸作为杂质的 N-保护-α-L-天冬氨酰-L-苯丙氨酸溶液中选择性分离 N-保护-α-L-天冬氨酰-L-苯丙氨酸的工艺。
• Preparation of alpha-L-aspartyl-L-phenyl-alanine methyl ester or hydrohalide thereof
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0270345A2

  公开（公告）日：1988-06-08

  α-L-aspartyl-L-phenylalanine methyl ester or the hydrohalide thereof is prepared by esterifying α-L-aspartyl-L-phenylalanine or α-L-aspartyl-L-­phenylalanine which has been formed in situ by treating an N-protected-α-L-aspartyl-­L-phenylalanine in an aqueous solution of sulfuric acid or a methanol-containing aqueous solution of sulfuric acid in the presence of an alkali metal halide or alkaline earth metal halide in a medium composed of sulfuric acid, water and methanol, thereby to allow the resulting α-L-aspartyl-L-phenyl-alanine methyl ester to precipitate as its correspond­ing hydrohalide, and then isolating the hydrohalide; and when the preparation of the methyl ester is desired, neutralizing the hydrohalide.

  α-L-天冬氨酰-L-苯丙氨酸甲酯或其氢卤化物的制备方法是：在碱金属卤化物或碱土金属卤化物存在的情况下，将α-L-天冬氨酰-L-苯丙氨酸或α-L-天冬氨酰-L-苯丙氨酸在硫酸水溶液或含甲醇的硫酸水溶液中进行酯化。L-苯丙氨酸在硫酸水溶液或含甲醇的硫酸水溶液中，在碱金属卤化物或碱土金属卤化物存在下，在由硫酸组成的介质中形成、水和甲醇，从而使生成的 α-L-天冬氨酰-L-苯丙氨酸甲酯沉淀为其相应的氢卤化物，然后分离氢卤化物；当需要制备甲酯时，中和氢卤化物。