N^α-acetyl-5-fluoro-D,L-tryptophan | 7303-54-0

• 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^α-acetyl-5-fluoro-D,L-tryptophan
• 英文别名: Ac-5'-F-Trp-OH；N^α-acetyl-5-fluoro-DL-tryptophan；N^α-Acetyl-5-fluor-DL-tryptophan；N-Acetyl-5-fluoro-DL-tryptophan；2-acetamido-3-(5-fluoro-1H-indol-3-yl)propanoic acid
• CAS: 7303-54-0
• 化学式: C₁₃H₁₃FN₂O₃
• 分子量: 264.256
• InChiKey: KRMRBEXBEPMAQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N^α-acetyl-5-fluoro-D,L-tryptophan 在 cobalt(II) chloride hexahydrate 、 porcine kidney L-acylase 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.34h， 生成 Ac-5-F-D-Trp-Phe-Gly-NH₂
  参考文献：
  名称：

  Synthesis of Tripeptides Containing d-Trp Substituted at the Indole Ring, Assessment of Opioid Receptor Binding and in Vivo Central Antinociception

  摘要：

  The noncationizable tripeptide Ac-D-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of D-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.

  DOI：

  10.1021/jm5002925
• 作为产物：
  描述：

  acetylamino-(5-fluoro-indol-3-ylmethyl)-malonic acid diethyl ester 在 sodium hydroxide 、 水 作用下， 生成 N^α-acetyl-5-fluoro-D,L-tryptophan
  参考文献：
  名称：

  The Synthesis of 5-Fluoro-DL-tryptophan

  摘要：

  DOI：

  10.1021/ja01161a523

文献信息

• The facile synthesis of a series of tryptophan derivatives
  作者：Georg Blaser、John M. Sanderson、Andrei S. Batsanov、Judith A.K. Howard

  DOI：10.1016/j.tetlet.2008.02.120

  日期：2008.4

  of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions

  这项研究报告了一种简便的方法，用于合成各种5和6取代的色氨酸衍生物，这些色素很难使用替代酶方法制备。原位衍生自丝氨酸的活化氨基酸的酰化与酶促拆分步骤相结合，以提供带有一系列吸电​​子和释放电子的取代基的对映纯类似物。从某些反应中分离出作为副产物的脱氢丙氨酸衍生物，可为该反应的可能机理提供一些见解。
• 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：——
• [EN] NOVEL GLUTAMINE ANALOGS<br/>[FR] NOUVEAUX ANALOGUES DE GLUTAMINE
  申请人：[en]JACOBIO PHARMACEUTICALS CO., LTD.

  公开号：WO2022078462A1

  公开（公告）日：2022-04-21

  Glutamine analogs are provided, a composition containing the glutamine analogs and the use thereof.
• [EN] SMALL MOLECULE INHIBITORS OF THE CRL4 UBIQUITIN LIGASE<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE L'UBIQUITINE LIGASE CRL4
  申请人：[en]CORNELL UNIVERSITY

  公开号：WO2023173136A2

  公开（公告）日：2023-09-14

  Compounds of formula (I), compounds of formula (II), and compounds of formula (III) are disclosed. Also disclosed are compounds, compositions, and methods to inhibit CUL4A expression or activity, CUL4B expression or activity, and/or DDB1 expression or activity for the treatment or prevention of cancer, DNA damage, or related conditions. In some aspects, the interaction between CUL4A and/or CUL4B and the beta-propeller B of DDB1 is disrupted with the compounds, compositions, or methods.
• The Synthesis of 5-Fluoro-DL-tryptophan
  作者：Heinrich Rinderknecht、Carl Niemann

  DOI：10.1021/ja01161a523

  日期：1950.5