N-(4-phenylbutyroyl)-L-phenylalanine | 86432-34-0

• 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-(4-phenylbutyroyl)-L-phenylalanine
• 英文别名: N-(4-Phenylbutanoyl)-L-phenylalanine；(2S)-3-phenyl-2-(4-phenylbutanoylamino)propanoic acid
• CAS: 86432-34-0
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: WBHNICNVNQAUMP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-苯丙氨酸 、 4-苯基丁酰氯 在 sodium hydroxide 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以54.6%的产率得到N-(4-phenylbutyroyl)-L-phenylalanine
  参考文献：
  名称：

  Effect of Enzyme–Substrate Interactions Away from the Reaction Site on Carboxypeptidase A Catalysis

  摘要：

  The kinetics of 14 peptide substrates of carboxypeptidase A have been studied for the purpose of evaluating P-1-P-3/S-1-S-3 interactions. It was found that the amide group at P-1-P-2 is required for efficient catalysis. This observation is consistent with previously proposed hydrogen bonding interactions, based on crystallographic data, between the P-1 NH and Tyr-248 and between the P-2 carbonyl oxygen and Arg-71. In contrast, substitution of the benzamido amide group (at P-2-P-3) Of N-benzoylglycylglycyl-1-phenylalanine by -CH2CH2- resulted in more effective catalysis. In this case hydrophobic interactions are important in the ground state and in the transition state of the rate-determining step. (C) 1996 Academic Press. Inc.

  DOI：

  10.1006/bioo.1996.0026

文献信息

• Pharmaceutical composition having an excellent absorption property
  申请人：Ajinomoto Company Incoporated

  公开号：US04650785A1

  公开（公告）日：1987-03-17

  A compound represented by the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, a fluorine atom, a nitro group, a hydroxyl group or a hydroxyl group protected by an esterifying group; X is CO or SO.sub.2 ; --Y-- is a straight bond, a lower alkylene group, a substituted or unsubstituted vinylene group, or group having the formula --CH.sub.2 --O-- or --O--CH.sub.2 --; R.sup.2 is a substituted or unsubstituted phenyl or naphthyl group, or R.sup.2 --Y--CO is N-benzyloxycarbonylphenylalanyl, N-benzyloxycarbonyl-4-fluorophenylalanyl or N-(m-methoxycinnamoyl)-phenylalanyl group; or a non-toxic salt thereof is disclosed along with pharmaceutical compositions containing these compounds and methods of using these compositions to increase the rate of absorption of medicines.

  公开了一种由以下式表示的化合物：##STR1##其中R.sup.1是氢原子、氟原子、硝基、羟基或由酯化基团保护的羟基；X是CO或SO.sub.2；--Y--是直链键、较低的烷基链、取代或未取代的乙烯基链，或具有式--CH.sub.2 --O--或--O--CH.sub.2 --的基团；R.sup.2是取代或未取代的苯基或萘基，或R.sup.2 --Y--CO是N-苄氧羰基苯丙氨基、N-苄氧羰基-4-氟苯丙氨基或N-(m-甲氧基肉桂酰)-苯丙氨基基团；或其无毒盐，以及含有这些化合物的药物组合物和使用这些组合物以增加药物吸收速率的方法。
• Pharmaceutical composition
  申请人：AJINOMOTO CO., INC.

  公开号：EP0093551A2

  公开（公告）日：1983-11-09

  Phenylalinine derivatives having the general formula: and their non-toxic salts, have been found to promote the absorption of medicinal substances such as insulin. In the above formula, R' is a hydrogen atom, a fluorine atom, a nitro group, a hydroxyl group or a hydroxyl group protected by an esterifying group, X is -CO- or -SO2-, -Y- is a straight bond, a lower alkylene group, a substituted or unsubstituted vinylene group, or a group having the form- fula -CH2-O- or -0-CH2-, and R2 is a substituted or unsubstituted phenyl or naphthyl group; or the group R2-Y-CO- is an N-benzyloxy-carbonylphenylalanyl group, an N-benzyloxycarbonyl-4-flurophenylalanyl group or an N-(m-methoxycinnamoyl)phenylalanyl group.

  具有通式的苯丙氨酸衍生物 及其无毒盐，已被发现可促进胰岛素等药物的吸收。在上式中，R'是氢原子、氟原子、硝基、羟基或被酯化基保护的羟基，X 是-CO-或-SO2-，-Y-是直键、低级亚烷基、取代或未取代的亚乙烯基或具有-CH2-O-或-0-CH2-形式的基团，R2 是取代或未取代的苯基或萘基；或基团 R2-Y-CO- 是 N-苄氧羰基苯丙氨酰基团、N-苄氧羰基-4-氟苯丙氨酰基团或 N-（间甲氧基肉桂酰基）苯丙氨酰基团。
• US4650785A
  申请人：——

  公开号：US4650785A

  公开（公告）日：1987-03-17
• US4670584A
  申请人：——

  公开号：US4670584A

  公开（公告）日：1987-06-02
• Effect of Enzyme–Substrate Interactions Away from the Reaction Site on Carboxypeptidase A Catalysis
  作者：John F. Sebastian、Guiqing Liang、Annissa Jabarin、Karen Thomas、H.Bonnie Wu

  DOI：10.1006/bioo.1996.0026

  日期：1996.9

  The kinetics of 14 peptide substrates of carboxypeptidase A have been studied for the purpose of evaluating P-1-P-3/S-1-S-3 interactions. It was found that the amide group at P-1-P-2 is required for efficient catalysis. This observation is consistent with previously proposed hydrogen bonding interactions, based on crystallographic data, between the P-1 NH and Tyr-248 and between the P-2 carbonyl oxygen and Arg-71. In contrast, substitution of the benzamido amide group (at P-2-P-3) Of N-benzoylglycylglycyl-1-phenylalanine by -CH2CH2- resulted in more effective catalysis. In this case hydrophobic interactions are important in the ground state and in the transition state of the rate-determining step. (C) 1996 Academic Press. Inc.