β-Dioxindolyl-DL-alanin | 13081-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: β-Dioxindolyl-DL-alanin
• 英文别名: α-Dioxindolyl-DL-alanin；α-Dioxindolyl-L-alanin; β-Dioxindolyl-L-alanin；2-amino-3-(3-hydroxy-2-oxo-2,3-dihydro-indol-3-yl)-propionic acid；2-amino-3-(3-hydroxy-2-oxo-indolin-3-yl)-propionic acid；2-Amino-3-(3-hydroxy-2-oxo-indolin-3-yl)-propionsaeure；Dioxindolyl-l-alanine；2-amino-3-(3-hydroxy-2-oxo-1H-indol-3-yl)propanoic acid
• CAS: 13081-15-7
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: BZRCOYDQHJWPQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  564.5±50.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-Dioxindolyl-DL-alanin 生成 (3S)-3-hydroxyoxytryptophan
  参考文献：
  名称：

  Preparative separation of the diastereoisomers of dioxindolyl-L-alanine and assignment of stereochemistry at C-3

  摘要：

  DOI：

  10.1021/jo00303a027
• 作为产物：
  描述：

  2-hydroxyimino-3-(2-oxo-indolin-3-yl)-propionic acid 在 甲醇 、 sodium hydroxide 、 碘 、 钯 作用下， 生成 β-Dioxindolyl-DL-alanin
  参考文献：
  名称：

  Studies in the Indole Series. XVI.¹ Oxindole-3-alanine and Dioxindole-3-alanine

  摘要：

  DOI：

  10.1021/ja01595a064

文献信息

• Oxidative transformation of tryptophan to 3-(2-aminophenyl)-2-pyrrolidone and kynurenine
  作者：M. Nakagawa、S. Kato、H. Fukazawa、Y. Hasegawa、J. Miyazawa、T. Hino

  DOI：10.1016/s0040-4039(00)98249-2

  日期：1985.1

  Oxytryptophans 3, which are readily obtained by dye-sensitized photooxygenation of tryptophan followed by acid treatment, undergo a facile N,N′-transacylation to give the 3-(2-aminophenyl)-2-pyrrolidones 4 in the absence of oxygen, whereas in the presence of oxygen 3a was oxidized to kynurenine.

  氧色氨酸3很容易通过色氨酸的染料敏化光氧合，然后进行酸处理而获得，在不存在氧的情况下，容易进行N，N'-酰化反应，生成3-（2-氨基苯基）-2-吡咯烷酮4，而在氧气存在下，3a被氧化为犬尿氨酸。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• The decomposition of tryptophan in acid solutions: Specific effect of hydrochloric acid.
  作者：TAKAFUMI OHTA、SHIZUO SUZUKI、MIHO TODO、TSUTAO KURECHI

  DOI：10.1248/cpb.29.1767

  日期：——

  The stability of tryptophan in aqueous solutions of HCl, H2SO4, or CH3SO3H under aerobic conditions was examined, and a specific effect of HCl was found. A kinetic study of the HCl-induced decomposition, tests for the free chlorine formation on heating the HCl used for the above run, etc. suggested that free chlorine produced by the air oxidation of HCl may hace participated in the decomposition of tryptophan. Thin-layer and ion-exchange chromatography of the decomposition products of tryptophan revealed that oxindolylalanine and dioxindolylalanine were formed by the reaction. These two compounds were also formed by treating tryptophan with ClO- or N-chlorosuccinimide in a solution of HCl. These results support the above possibility.

  在有氧条件下，研究了色氨酸在 HCl、H2SO4 或 CH3SO3H 水溶液中的稳定性，发现 HCl 有特定的影响。对盐酸诱导分解的动力学研究、对上述实验所用盐酸加热时游离氯形成的测试等表明，盐酸在空气中氧化产生的游离氯可能参与了色氨酸的分解。色氨酸分解产物的薄层色谱法和离子交换色谱法显示，反应生成了氧吲哚丙氨酸和二氧吲哚丙氨酸。在盐酸溶液中用 ClO- 或 N-氯代琥珀酰亚胺处理色氨酸也会生成这两种化合物。这些结果证明了上述可能性。
• Mass spectrometric analysis of oxidized tryptophan
  作者：Marco van de Weert、Fija M. Lagerwerf、Johan Haverkamp、Wigger Heerma

  DOI：10.1002/(sici)1096-9888(199809)33:9<884::aid-jms698>3.0.co;2-s

  日期：1998.9

  Oxindolylalanine and oxindolylalanine-containing peptides were prepared by treatment of tryptophan and tryptophan-containing peptides with mixtures of dimethyl sulfoxide and hydrochloric acid in acetic acid (DMSO-HCl-HAc). The reaction between tryptophan and DMSO-HCl-HAc was monitored by fast atom bombardment mass spectrometry (FAB-MS) and the proposed chlorotryptophan intermediate in the reaction was observed. Almost complete conversion of tryptophan to oxindolylalanine was obtained in reaction mixtures containing 3.75 M HCl when the reaction was performed in an open tube. A higher HCl concentration (5.5 M) and a closed reaction tube promoted the formation of by-products, such as dioxindolylalanine and 3-chlorooxindolylalanine. Extensive hydrolysis C-terminal of tryptophan was observed when tryptophan-containing peptides were treated with DMSO-HCl-HAc containing 5.5 M HCl, during which the tryptophan residue was modified to dioxindolylalanine lactone, Hydrolysis was not observed in mixtures containing 3.75 M HCl. The presence of oxindolylalanine in peptides could be demonstrated by characteristic peaks in FAB collision-induced dissociation tandem mass spectra. (C) 1998 John Wiley & Sons, Ltd.
• USE OF TRYPTOPHAN DERIVATIVES FOR PROTEIN FORMULATIONS
  申请人：Genentech, Inc.

  公开号：US20170239355A1

  公开（公告）日：2017-08-24

  The invention provides methods and formulations comprising a protein comprising solvent accessible amino acid residues susceptible to oxidation wherein N-acetyl tryptophan (NAT) is used to prevent oxidation of the protein. The invention also provides methods for making such formulations and methods of using such formulations. Methods to measure degradation of NAT in protein formulations are also provided.