7-氟-L-色氨酸 | 138514-97-3

• 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: 7-氟-L-色氨酸
• 中文别名: L-7-氟色氨酸
• 英文名称: L-7-fluorotryptophan
• 英文别名: 7-fluoro-tryptophan；(S)-2-Amino-3-(7-fluoro-1H-indol-3-yl)propanoic acid；(2S)-2-amino-3-(7-fluoro-1H-indol-3-yl)propanoic acid
• CAS: 138514-97-3
• 化学式: C₁₁H₁₁FN₂O₂
• 分子量: 222.219
• InChiKey: ADMHYWIKJSPIGJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 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：
  4

安全信息

• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  室温、密闭保存，并保持干燥。

反应信息

• 作为反应物：
  描述：

  7-氟-L-色氨酸 在 ammonia borane 、 氧气 作用下， 以 aq. phosphate buffer 为溶剂， 反应 24.0h， 生成 3-(7-fluoro-1H-indol-3-yl)-2-hydroxypropanoic acid
  参考文献：
  名称：

  用卤代色氨酸调节RGD肽的生物活性†

  摘要：

  使用通过卤化酶的酶促卤化或使用色氨酸合酶掺入卤代吲哚来合成在吲哚部分具有不同取代基的1-和d-卤代色氨酸的阵列。将这些Trp衍生物引入RGD肽作为基准系统以研究其对生物活性的影响。含Halotryptophan-RGD肽显示增加的亲和力朝向整合素α v β 3和增强的过整合素α选择性5 β 1。另外，铃木色氨酸被铃木-宫浦交叉耦合（SMC）开发为后期多样化的平台，从而产生了新的自然的联芳基序。这些肽显示出增强的朝向α亲和力v β 3，良好的亲和力，以α v β 8，和显着的选择性超过α 5 β 1和α IIB β 3，同时具有荧光性质。在体外证明了其作为探针的可行性。进行了广泛的分子动力学模拟，以阐明这些后期多样化的环状RGD肽的NMR和高效液相色谱（HPLC）数据，并进一步表征其构象偏好。

  DOI：

  10.1021/acs.jmedchem.0c01536
• 作为产物：
  描述：

  3-(1-acetyl-7-fluoroindol-3-yl)-2-aminopropanoic acid 生成 7-氟-L-色氨酸
  参考文献：
  名称：

  Dimethylallyltryptophan synthase. An enzyme-catalyzed electrophilic aromatic substitution

  摘要：

  Dimethylallyltryptophan (DMAT) synthase catalyzes the alkylation of L-tryptophan at C(4) by dimethylallyl diphosphate (DMAPP) in the first pathway-specific step in the biosynthesis of ergot alkaloids. The mechanism of the reaction was studied with analogs of both substrates. Five 7-substituted derivatives of N-acetyltryptophan (2, Z = OCH3, CH3, F, CF3, and NO2) were synthesized. The L enantiomers of the free amino acids were obtained by selective hydrolysis of the racemate using aminoacylase from Aspergillus. In addition, the E and Z fluoromethyl and difluoromethyl analogs of DMAPP (1, Y = CH3, CH2F, CHF2) were prepared. Rates of the enzyme-catalyzed reactions were measured for the dimethylallyl derivatives with L-tryptophan and for the L-tryptophan derivatives with DMAPP. In addition, the relative reactivities of the methanesulfonate derivatives of the DMAPP analogs were determined for solvolysis in aqueous acetone. A Hammett plot for the tryptophan analogs gave a good linear correlation with rho = -2.0. In addition, a Hammett plot of the logarithms of the relative rates of solvolysis and enzyme-catalyzed alkylation gave a positive linear correlation. These results indicate that the prenyl-transfer reaction catalyzed by DMAT synthase is an electrophilic aromatic substitution and is mechanistically similar to the electrophilic alkylation catalyzed by farnesyl diphosphate synthase.

  DOI：

  10.1021/ja00045a004

文献信息

• [EN] RAS BINDING PEPTIDES AND METHODS OF USE<br/>[FR] PEPTIDES DE LIAISON À RAS ET MÉTHODES D'UTILISATION
  申请人：RA PHARMACEUTICALS INC

  公开号：WO2017181061A1

  公开（公告）日：2017-10-19

  The present invention provides Ras modulators including inhibitors and/or antagonists of Ras, Ras binding, and Ras-dependent cell signaling activity. Also provided are methods of utilizing the Ras modulators as therapeutics.

  本发明提供了Ras调节剂，包括Ras的抑制剂和/或拮抗剂，以及Ras结合和Ras依赖的细胞信号活性。还提供了利用这些Ras调节剂作为治疗药物的方法。
• Inhibitors of cellular necrosis
  申请人：Cuny D. Gregory

  公开号：US20050119260A1

  公开（公告）日：2005-06-02

  The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.

  本发明涉及化合物、药物制剂及其在预防或治疗与细胞死亡相关的创伤、缺血、中风和退行性疾病中的应用的治疗。本发明的方法和组合物特别适用于治疗与细胞坏死相关的神经系统疾病。
• [EN] HIGHLY ACTIVE SELF-SUFFICIENT NITRATION BIOCATALYSTS<br/>[FR] BIOCATALYSEURS DE NITRATION AUTO-SUFFISANTS HAUTEMENT ACTIFS
  申请人：UNIV FLORIDA

  公开号：WO2018081456A1

  公开（公告）日：2018-05-03

  The disclosure relates to the field of fusion proteins. In some aspects, the disclosure relates to artificial fusion proteins comprising cytochrome P450 enzymes linked to reductase enzymes and uses thereof. In some aspects, the disclosure relates to compounds produced by artificial cytochrome P450 enzymes.

  该披露涉及融合蛋白的领域。在某些方面，该披露涉及人工融合蛋白，其中包括与还原酶酶相连的细胞色素P450酶，并其用途。在某些方面，该披露涉及由人工细胞色素P450酶产生的化合物。
• INHIBITORS OF CELLULAR NECROSIS
  申请人：Cuny Gregory D.

  公开号：US20120149702A1

  公开（公告）日：2012-06-14

  The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.

  本发明涉及化合物和药物制剂及其在预防或治疗与细胞死亡相关的创伤、缺血、中风和退行性疾病中的应用。本发明的方法和组合物特别适用于治疗与细胞坏死相关的神经系统疾病。
• L-tryptophan-producing microorganisms
  申请人：AJINOMOTO CO., INC.

  公开号：EP0080378A2

  公开（公告）日：1983-06-01

  L-tryptophan producing microorganisms are constructed by incorporating, into a recipient strain of the genus Bacillus, a recombinant plasmid containing a DNA fragment controlling resistance to a tryptophan-antagonist, which DNA fragment is obtained from chromosal DNA of a mutantof the genus Bacillus resistant to the tryptophan-antagonist.

  将含有控制对色氨酸拮抗剂抗性的 DNA 片段的重组质粒加入芽孢杆菌属的受体菌株中，就能构建生产 L-色氨酸的微生物，该 DNA 片段是从对色氨酸拮抗剂具有抗性的芽孢杆菌属突变体的染色质 DNA 中获得的。