5-氯色氨酸 | 55325-48-9

• 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
• 中文名称: 5-氯色氨酸
• 中文别名: 5-氯-D-色氨酸
• 英文名称: D-5-chlorotryptophan
• 英文别名: (2R)-2-azaniumyl-3-(5-chloro-1H-indol-3-yl)propanoate
• CAS: 55325-48-9
• 化学式: C₁₁H₁₁ClN₂O₂
• 分子量: 238.674
• InChiKey: TUKKZLIDCNWKIN-SECBINFHSA-N

物化性质

• 沸点：
  476.9±45.0 °C(Predicted)
• 密度：
  1.474±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-氯色氨酸 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 18.5h， 生成 (3R)-6-chloro-2-methylsulfanylcarbothioyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of 1,2,3,4-tetrahydro-.BETA.-carboline derivatives as hepatoprotective agents. III. Introduction of substituents onto methyl 1,2,3,4-tetrahydro-.BETA.-carboline-2-carbodithioate.

  摘要：

  合成了多种取代四氢-β-吲哚-二硫代氨基甲酸盐，并测试了其在小鼠中对四氯化碳 (CCl4) 诱导的肝损伤的肝保护活性。研究了结构-活性关系。3位取代基与二硫代氨基甲酸盐基团的相邻基团参与似乎对活性的体现非常重要。在3位具有亲水性取代基的化合物（1a、2a 和 3i）表现出了显著的活性。在3-羧酸（1a）的9位进行取代则降低了活性。

  DOI：

  10.1248/cpb.35.3284
• 作为产物：
  描述：

  5-氯-DL-色氨酸 在 IvoA acetyltransferase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  Complete Stereoinversion of l-Tryptophan by a Fungal Single-Module Nonribosomal Peptide Synthetase

  摘要：

  Single-module nonribosomal peptide synthetases (NRPSs) and NRPS-like enzymes activate and transform carboxylic acids in both primary and secondary metabolism and are of great interest due to their biocatalytic potentials. The single-module NRPS IvoA is essential for fungal pigment biosynthesis. Here, we show that IvoA catalyzes ATP-dependent unidirectional stereo inversion of L-tryptophan to D-tryptophan with complete conversion. While the stereoinversion is catalyzed by the epimerization (E) domain, the terminal condensation (C) domain stereoselectively hydrolyzes D-tryptophanyl-S-phosphopantetheine thioester and thus represents a noncanonical C domain function. Using IvoA, we demonstrate a biocatalytic stereoinversion/deracemization route to access a variety of substituted D-tryptophan analogs in high enantiomeric excess.

  DOI：

  10.1021/jacs.9b08898

文献信息

• COMPOUNDS AND METHOD OF USE
  申请人：Ferro Therapeutics, Inc.

  公开号：US20190263802A1

  公开（公告）日：2019-08-29

  This present disclosure relates to compounds with ferroptosis inducing activity, a method of treating a subject with cancer with the compounds, and combination treatments with a second therapeutic agent.

  本公开涉及具有诱导铁死亡活性的化合物，一种使用这些化合物治疗癌症患者的方法，以及与第二种治疗药物的联合治疗。
• PORTER, JOHN;DYKERT, JOHN;RIVIER, JEAN, INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 1, 13-21
  作者：PORTER, JOHN、DYKERT, JOHN、RIVIER, JEAN

  DOI：——

  日期：——
• SAIGA, YUTAKA;IIJIMA, IKUO;ISHIDA, AKIHIKO;MIYAGISHIMA, TOSHIKAZU;HOMMA, +, CHEM. AND PHARM. BULL., 35,(1987) N 8, 3284-3291
  作者：SAIGA, YUTAKA、IIJIMA, IKUO、ISHIDA, AKIHIKO、MIYAGISHIMA, TOSHIKAZU、HOMMA, +

  DOI：——

  日期：——
• Complete Stereoinversion of <scp>l</scp>-Tryptophan by a Fungal Single-Module Nonribosomal Peptide Synthetase
  作者：Yang Hai、Matthew Jenner、Yi Tang

  DOI：10.1021/jacs.9b08898

  日期：2019.10.16

  Single-module nonribosomal peptide synthetases (NRPSs) and NRPS-like enzymes activate and transform carboxylic acids in both primary and secondary metabolism and are of great interest due to their biocatalytic potentials. The single-module NRPS IvoA is essential for fungal pigment biosynthesis. Here, we show that IvoA catalyzes ATP-dependent unidirectional stereo inversion of L-tryptophan to D-tryptophan with complete conversion. While the stereoinversion is catalyzed by the epimerization (E) domain, the terminal condensation (C) domain stereoselectively hydrolyzes D-tryptophanyl-S-phosphopantetheine thioester and thus represents a noncanonical C domain function. Using IvoA, we demonstrate a biocatalytic stereoinversion/deracemization route to access a variety of substituted D-tryptophan analogs in high enantiomeric excess.
• Synthesis of 1,2,3,4-tetrahydro-.BETA.-carboline derivatives as hepatoprotective agents. III. Introduction of substituents onto methyl 1,2,3,4-tetrahydro-.BETA.-carboline-2-carbodithioate.
  作者：YUTAKA SAIGA、IKUO IIJIMA、AKIHIKO ISHIDA、TOSHIKAZU MIYAGISHIMA、KOICHI HOMMA、TOKURO OH-ISHI、MAMORU MATSUMOTO、YUZO MATSUOKA

  DOI：10.1248/cpb.35.3284

  日期：——

  Dithiocarbamates of various substituted tetrahydro-β-carbolines were synthesized and tested for hepatoprotective activity against carbon tetrachloride (CCl4) -induced liver damage in mice. Structure-activity relationships were investigated. Some neighboring group participation of the 3-substituent with the dithiocarbamate group appeared to be important for the manifestation of activity. The compounds (1a, 2a, and 3i) with hydrophilic substituents at the 3 poisition exhibited significant activity. Substitution at the 9 position of the 3-carboxylic acid (1a) lowered the activity.

  合成了多种取代四氢-β-吲哚-二硫代氨基甲酸盐，并测试了其在小鼠中对四氯化碳 (CCl4) 诱导的肝损伤的肝保护活性。研究了结构-活性关系。3位取代基与二硫代氨基甲酸盐基团的相邻基团参与似乎对活性的体现非常重要。在3位具有亲水性取代基的化合物（1a、2a 和 3i）表现出了显著的活性。在3-羧酸（1a）的9位进行取代则降低了活性。