Boc-Phe-Phe-Trp-OMe | 54613-87-5

• 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: Boc-Phe-Phe-Trp-OMe
• 英文别名: Boc-Phe-Phe-Trp-OCH3；methyl (2S)-3-(1H-indol-3-yl)-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]propanoate
• CAS: 54613-87-5
• 化学式: C₃₅H₄₀N₄O₆
• 分子量: 612.726
• InChiKey: ZZOSKRQSYURYPB-DTXPUJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Phe-Trp-OMe 在 N-甲基吗啉 、 盐酸 、 氢氟酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二甲基硫 、 乙酸乙酯 、 苯甲醚 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 22.0h， 生成 N-((3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxyl)-Phe-Phe-Trp
  参考文献：
  名称：

  Novel β-carboline-tripeptide conjugates attenuate mesenteric ischemia/reperfusion injury in the rat

  摘要：

  We have synthesized a series of new beta-carboline-tripeptide conjugates, and examined their anti-inflammatory properties in a mouse model of xylene-induced ear edema. The analgesic capacity of these compounds was further evaluated in a rodent tail flick assay. Our results indicate that beta-carboline conjugate 4a manifests potent anti-inflammatory and analgesic activity while exerting a protective effect against mesenteric ischemia/reperfusion (I/R) injury in the rat. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.03.029

文献信息

• Late-Stage Photoredox C–H Amidation of N-Unprotected Indole Derivatives: Access to <i>N</i>-(Indol-2-yl)amides
  作者：Yue Weng、Bo Ding、Yunqing Liu、Chunlan Song、Lo-Ying Chan、Chien-Wei Chiang

  DOI：10.1021/acs.orglett.1c00609

  日期：2021.4.2

  carboxamides are valuable in pharmaceutical applications, the preparation N-(indol-2-yl)amides with similar structures continues to be challenging. Herein we report on visible-light-induced late-stage photoredox C–H amidation with N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. N-Unprotected indoles and aryloxyamides that contain an electron-withdrawing

  N-未保护的吲哚的后期功能化可用于修饰低分子量药物和生物活性肽。吲哚羧酰胺在医药应用中很有价值，而具有相似结构的N-（吲哚-2-基）酰胺的制备仍然具有挑战性。本文中我们报道了可见光诱导的后期光氧化还原C–H酰胺化与N-未保护的吲哚和含色氨酸的肽，导致N的形成-（吲哚-2-基）酰胺衍生物。通过在室温下用绿色发光二极管照射，可以将含有吸电子基团的N-未保护的吲哚和芳氧基酰胺直接偶联至曙红Y作为光催化剂。机理研究和密度泛函理论计算表明，这种转变可能通过吲哚从PS *到PS •–循环的C–H氧化功能化而进行。该协议为N-未保护的吲哚衍生物的后期修饰标记和肽-药物结合提供了一个新的工具包。
• Selective Photoredox Trifluoromethylation of Tryptophan-Containing Peptides
  作者：Bo Ding、Yue Weng、Yunqing Liu、Chunlan Song、Le Yin、Jiafan Yuan、Yanrui Ren、Aiwen Lei、Chien-Wei Chiang

  DOI：10.1002/ejoc.201901572

  日期：2019.12.15

  visible‐light‐induced bioconjugation of tryptophan‐containing peptides using of photoredox catalysis is described. The trifluoromethylation proceeds under mild, biocompatible, and straightforward conditions. Using this strategy, the trifluoromethyl group could be incorporated into tryptophan residue with excellent chemo‐ and site‐selectivity.

  描述了使用光氧化还原催化的色氨酸肽的可见光生物共轭。三氟甲基化在温和的，生物相容的和直接的条件下进行。使用这种策略，可以将三氟甲基结合到色氨酸残基中，具有出色的化学和位点选择性。
• Novel β-carboline-tripeptide conjugates attenuate mesenteric ischemia/reperfusion injury in the rat
  作者：Wei Bi、Yue Bi、Ping Xue、Yanrong Zhang、Xiang Gao、Zhibo Wang、Meng Li、Michele Baudy-Floc’h、Nathaniel Ngerebara、Xiaoxu Li、K. Michael Gibson、Lanrong Bi

  DOI：10.1016/j.ejmech.2011.03.029

  日期：2011.6

  We have synthesized a series of new beta-carboline-tripeptide conjugates, and examined their anti-inflammatory properties in a mouse model of xylene-induced ear edema. The analgesic capacity of these compounds was further evaluated in a rodent tail flick assay. Our results indicate that beta-carboline conjugate 4a manifests potent anti-inflammatory and analgesic activity while exerting a protective effect against mesenteric ischemia/reperfusion (I/R) injury in the rat. Published by Elsevier Masson SAS.