acetyl-5-bromo-DL-tryptophan | 75816-15-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 色氨酸类衍生物
• 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: acetyl-5-bromo-DL-tryptophan
• 英文别名: N^α-acetyl-5-bromo-D,L-tryptophan；Ac-5'-Br-Trp-OH；(RS)-Ac-5-BrTrp-OH；N-acetyl-5-bromo-DL-Trp；3-(5-bromo-1H-indol-3-yl)-2-acetamidopropanoic acid；2-acetamido-3-(5-bromo-1H-indol-3-yl)propanoic acid
• CAS: 75816-15-8
• 化学式: C₁₃H₁₃BrN₂O₃
• mdl: MFCD09756739
• 分子量: 325.162
• InChiKey: IMYCFTBQVUCEKW-UHFFFAOYSA-N

物化性质

• 熔点：
  201-204 °C
• 沸点：
  627.7±55.0 °C(Predicted)
• 密度：
  1.615±0.06 g/cm3(Predicted)

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：
  3

反应信息

• 作为反应物：
  描述：

  acetyl-5-bromo-DL-tryptophan 在 cobalt(II) chloride hexahydrate 、 acylase I from porcine kidney 作用下， 以 aq. phosphate buffer 为溶剂， 反应 108.0h， 以20%的产率得到(2S)-2-氨基-3-(5-溴-1H-吲哚-3-基)丙酸
  参考文献：
  名称：

  Discovery of 7-[¹⁸F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo

  摘要：

  Tryptophan and its metabolites are involved in different physiological and pathophysiological processes. Consequently, positron emission tomography (PET) tracers addressing tryptophan metabolic pathways should allow the detection of different pathologies like neurological disorders and cancer. Herein we report an efficient method for the preparation of fluorotryptophans labeled in different positions with F-18 and their biological evaluation. 4-7-[F-18]Fluorotryptophans ([F-18]FTrps) were prepared according to a modified protocol of alcohol-enhanced Cu-mediated radiofluorination in 30-53% radiochemical yields. In vitro experiments demonstrated high cellular uptake of 4-7[F-18]FTrps in different tumor cell lines. 4, 5-, and 6-[F-18]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[F-18]FTrp demonstrated a high in vivo stability and enabled a clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains. Moreover 7-[F-18]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[F-18]FTrp represents a highly promising PET probe for imaging of Trp metabolism.

  DOI：

  10.1021/acs.jmedchem.7b01245
• 作为产物：
  描述：

  5-bromo-3-<2-acetamido-2,2-bis(ethoxycarbonyl)ethyl>indole 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 3.5h， 生成 acetyl-5-bromo-DL-tryptophan
  参考文献：
  名称：

  5-和7-溴色氨酸和[5-溴色氨酸9 ]-β-促肾上腺皮质激素-（1-24）-四糖肽的合成，一种高效的促肾上腺皮质激素类似物

  摘要：

  描述了通过4-乙酰氨基-4,4-双（乙氧基羰基）丁醛的适当溴苯phenyl的费歇尔环化的5-溴-L-色氨酸和7-溴-L-色氨酸的合成。使用逐步和片段缩合的标准方法合成标题四糖肽。通过酸性或酶水解后的氨基酸分析和高压液相色谱法判断产物是纯的。在分离的肾上腺细胞生物测定中，该肽的类固醇生成能力是Synacthen的2.4倍。

  DOI：

  10.1039/p19800001928

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。
• Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor
  作者：Michio Kuruma、Taiki Suzuki、Yoshiya Seto

  DOI：10.1016/j.bmcl.2021.128085

  日期：2021.7

  post-radicle growth of O. minor. We designed a hybrid chemical (13), in which IAA is attached to a part of SL, and found that this synthetic analog induced the germination of O. minor, and also inhibited post-radicle growth. Moreover, contrary to our expectations, we found that N-acetyl Trp (9) showed germination stimulating activity, and introduction of a substitution at C-5 position increased its activity

  根寄生植物萌发由宿主衍生的化学物质独脚金内酯 (SL) 诱导。我们发现主要的微生物培养液成分胰蛋白胨抑制根寄生植物Orobanche minor的 SL 诱导萌发。从色氨酸中分离出作为活性化合物的l -色氨酸 ( l -Trp)。我们进一步发现l- Trp 相关化合物 ( 1b - 11 )，如主要的植物激素生长素 ( 8，indole-3-乙酸；IAA)，也抑制O. minor的萌发和胚根后生长。我们设计了一种混合化学品（13)，其中 IAA 连接到 SL 的一部分，并发现这种合成类似物诱导了O. minor的萌发，也抑制了胚根后的生长。此外，与我们的预期相反，我们发现N-乙酰 Trp ( 9 ) 显示出萌发刺激活性，并且在 C-5 位置引入取代增加了其活性 ( 12a - 12f )。我们的数据，特别是发现具有两种活性的结构杂化化合物，可诱导自发发芽和抑制随后的自由基生长，将为根寄生植物提供新型发芽调节剂。
• Synthesis of Tripeptides Containing <scp>d</scp>-Trp Substituted at the Indole Ring, Assessment of Opioid Receptor Binding and in Vivo Central Antinociception
  作者：Rossella De Marco、Andrea Bedini、Santi Spampinato、Luca Gentilucci

  DOI：10.1021/jm5002925

  日期：2014.8.14

  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.
• Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors
  作者：Minoru Tanaka、Xin Li、Hidemasa Hikawa、Takafumi Suzuki、Katsuhiko Tsutsumi、Masashi Sato、Osamu Takikawa、Hideharu Suzuki、Yuusaku Yokoyama

  DOI：10.1016/j.bmc.2012.12.028

  日期：2013.3

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.
• 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：——