N-Hydroxytryptophan | 87843-31-0

• 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: N-Hydroxytryptophan
• 英文别名: 2-(hydroxyamino)-3-(1H-indol-3-yl)propanoic acid
• CAS: 87843-31-0
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: PNBGTYVVHKDDFM-UHFFFAOYSA-N

物化性质

• 沸点：
  529.8±60.0 °C(Predicted)
• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.4
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Hydroxytryptophan 生成 3-吲哚乙酸
  参考文献：
  名称：

  RAJAGORAL, RANGANATNA;MZHUSTOOLLER, IV.;OLSEN, CARL ERIK, PHYTOCHEMISTRY, 30,(1991) N, C. 1405-1408

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(3-吲哚基)-2-氧代丙酸 在 羟胺 、 sodium cyanoborohydride 作用下， 生成 N-Hydroxytryptophan
  参考文献：
  名称：

  Synthesis, biological activity and metabolism of N-hydroxytryptophan

  摘要：

  N-Hydroxytryptophan (alpha-hydroxyamino-beta-indolyl-3-propionic acid) was chemically synthesized. On a mole basis, its relative biological activity in comparison with indole-3-acetic acid at sub-optimal concentrations is: oat coleoptile curvature test = 0.129; oat first internode test = 0.089 and linseed root growth inhibition test = 0.022. Infiltration of N-hydroxytryptophan into oat coleoptile sections leads to the production of indoleacetaldehyde oxime, indoleacetaldehyde and indoleacetic acid. It is suggested that tryptophan could be metabolized in oat coleoptiles to indole-3-acetic acid via N-hydroxytryptophan, indoleacetaldehyde oxime and indoleacetaldehyde.

  DOI：

  10.1016/0031-9422(91)84174-q

文献信息

• [EN] AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS CD36 À BASE D'AZASULFURYLPEPTIDES ET UTILISATIONS DE CEUX-CI
  申请人：RSEM LTD PARTNERSHIP

  公开号：WO2016029324A1

  公开（公告）日：2016-03-03

  Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.

  揭示了能够抑制CD36活性的新型含氮硫酰基的肽类模拟物。还揭示了利用这些含氮硫酰基的肽类模拟物治疗与CD36相关的疾病、紊乱或状况，包括TLR2介导的炎症性疾病、紊乱或状况的用途，以及获取这种含氮硫酰基的肽类模拟物的方法。
• [EN] METHODS FOR PRODUCING D-TRYPTOPHAN AND SUBSTITUTED D-TRYPTOPHANS<br/>[FR] PROCÉDÉS DE PRODUCTION DE D-TRYPTOPHANE ET DE D-TRYPTOPHANES SUBSTITUÉS
  申请人：UNIV CALIFORNIA

  公开号：WO2021055696A1

  公开（公告）日：2021-03-25

  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. As disclosed herein, we show that IvoA catalyzes ATP-dependent unidirectional stereoinversion 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.

  单模块非核糖体肽合酶（NRPSs）和类NRPS酶在初级和次级代谢中激活和转化羧酸，由于其生物催化潜力，备受关注。单模块NRPS IvoA 对真菌色素生物合成至关重要。正如本文所披露的，我们展示了IvoA 催化ATP依赖的L-色氨酸向D-色氨酸的单向立体反转，实现了完全转化。虽然立体反转由外消旋（E）结构域催化，但末端缩合（C）结构域具有立体选择性地水解D-色氨酰-S-磷酰巯基丝氨酸酯，因此代表了非规范的C结构域功能。利用IvoA，我们展示了一种生物催化的立体反转/去消旋途径，以获得多种取代D-色氨酸类似物，其旋光异构体过量达到高水平。
• [EN] NOVEL METHOD FOR SYNTHESIZING AMANITINS<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE D'AMANITINES
  申请人：HEIDELBERG PHARMA GMBH

  公开号：WO2019030171A1

  公开（公告）日：2019-02-14

  The invention relates to novel methods for synthesizing amanitin derivatives having an amino group attached to position 6' of the central tryptophan moiety. The invention furthermore relates to a novel amanitin derivative having an amino group attached to position 6' of the central tryptophan moiety, novel conjugates of such amanitin derivative, and pharmaceutical compositions comprising such conjugates.

  该发明涉及新的方法，用于合成在中心色氨酸部分6'位置带有氨基的鹅膏蕈碱衍生物。此外，该发明还涉及一种新的鹅膏蕈碱衍生物，其中心色氨酸部分6'位置带有氨基，以及这种鹅膏蕈碱衍生物的新结合物，以及包含这种结合物的药物组合物。
• [EN] ANTIBODY-DRUG CONJUGATES<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT
  申请人：SPIREA LTD

  公开号：WO2021240155A1

  公开（公告）日：2021-12-02

  The present invention relates to antibody-drug conjugates comprising (i) an antibody or antigen-binding fragment thereof, (ii) a polymer comprising a particular repeat unit comprising an amino acid derivative, which is covalently bound to one or more biologically active moieties, such as small molecule drugs, optionally via a linker, and (iii) a polymer-antibody linker moiety which is covalently bound to both the polymer and the antibody or antigen-binding fragment thereof. Additionally, the present invention relates to pharmaceutical compositions comprising the antibody-drug conjugates and to use of the antibody-drug conjugates in medicine.

  本发明涉及抗体-药物偶联物，包括（i）抗体或其抗原结合片段，（ii）聚合物，其中包括一个特定重复单元，该单元包括氨基酸衍生物，与一个或多个生物活性基团如小分子药物共价结合，可选地通过连接剂连接，以及（iii）聚合物-抗体连接基团，它们与聚合物和抗体或其抗原结合片段均共价结合。此外，本发明涉及包括抗体-药物偶联物的药物组合物以及在医学上使用抗体-药物偶联物。
• Covalent conjugates of biologically-active compounds with amino acids and amino acid derivatives for targeting to physiologically-protected sites
  申请人：——

  公开号：US20030087803A1

  公开（公告）日：2003-05-08

  This invention herein describes a method of facilitating the entry of drugs into cells and tissues at physiologically protected sites at pharmacokinetically useful levels and also a method of targeting drugs to physiologically protected sites in vivo. Also provided are drug conjugates with an amino acid or derivative thereof for facilitating such targeted drug delivery. The conjugates and methods of this invention provide an advance over other drug targeting methods known in the prior art, because the invention provides drug concentrations in such physiologically protected sites that can reach therapeutically-effective levels after administration of systemic levels much lower than are currently administered to achieve a therapeutic dose. This technology is appropriate for use with psychotropic, neurotropic, neurological, antibiotic, antibacterial, antimycotic, antiviral, antiproliferative or antineoplastic drugs, agents and conjugates, for rapid and efficient introduction of such agents across, e.g., the blood-brain barrier. Further, the invention provides means for retention and prolonged enzymatic release of such drugs, agents and conjugates comprising the conjugates of the invention, in the brain and central nervous system and other physiologically-protected sites.

  本发明描述了一种促进药物进入细胞和组织的方法，在生理保护部位以药代动力学有用的水平，并且描述了一种将药物靶向到体内生理保护部位的方法。还提供了带有氨基酸或其衍生物的药物共轭物，用于促进这种靶向药物传递。本发明的共轭物和方法相对于先前已知的其他药物靶向方法具有进步性，因为该发明提供了在这些生理保护部位的药物浓度，这些浓度可以在系统水平远低于目前用于达到治疗剂量的水平后达到治疗有效水平。这项技术适用于用于精神药物、神经药物、神经学药物、抗生素、抗菌药物、抗真菌药物、抗病毒药物、抗增殖或抗肿瘤药物、药剂和共轭物，用于快速高效地引入这些药剂跨越例如血脑屏障。此外，该发明提供了在大脑和中枢神经系统以及其他生理保护部位中保留和延长这些药物、药剂和共轭物的酶释放的手段。