Boc-3-iodo-L-tyrosine-3-iodo-L-tyrosine-OMe | 1373311-90-0

• 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: Boc-3-iodo-L-tyrosine-3-iodo-L-tyrosine-OMe
• 英文别名: N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester；Boc-Tyr(3-I)-Tyr(3-I)-OMe；methyl (2S)-3-(4-hydroxy-3-iodophenyl)-2-[[(2S)-3-(4-hydroxy-3-iodophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 1373311-90-0
• 化学式: C₂₄H₂₈I₂N₂O₇
• 分子量: 710.305
• InChiKey: FUYQQMHOLNJWQZ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-3-iodo-L-tyrosine-3-iodo-L-tyrosine-OMe 在 甲酸 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 五甲基苯 、 potassium carbonate 、 三氟乙酸 、 联硼酸频那醇酯 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 mycocyclosin
  参考文献：
  名称：

  Total Synthesis of Mycocyclosin

  摘要：

  The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an intramolecular Miyaura-Suzuki cross-coupling to generate the biaryl linkage.

  DOI：

  10.1021/ol300831t
• 作为产物：
  描述：

  L-酪氨酸 在 ammonium hydroxide 、 氯化亚砜 、 碘 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 Boc-3-iodo-L-tyrosine-3-iodo-L-tyrosine-OMe
  参考文献：
  名称：

  Total Synthesis of Mycocyclosin

  摘要：

  The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an intramolecular Miyaura-Suzuki cross-coupling to generate the biaryl linkage.

  DOI：

  10.1021/ol300831t

文献信息

• Structure–Activity Relationships of <i>cyclo</i>(<scp>l</scp>-Tyrosyl-<scp>l</scp>-tyrosine) Derivatives Binding to <i>Mycobacterium tuberculosis</i> CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct
  作者：Sunnia Rajput、Kirsty J. McLean、Harshwardhan Poddar、Irwin R. Selvam、Gayathri Nagalingam、James A. Triccas、Colin W. Levy、Andrew W. Munro、Craig A. Hutton

  DOI：10.1021/acs.jmedchem.9b01199

  日期：2019.11.14

  A series of analogues of cyclo(L-tyrosyl-L-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(L-tyrosyl-L-tyrosine) results in sub-mu M binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme Fe-III. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.
• Synthesis of Biphenyl Tyrosine Via Cross-Coupling Suzuki-Miyaura Reaction Using Aryltrifluoroborate Salts
  作者：Stanley N. S. Vasconcelos、Cristiane S. Barbeiro、Amna N. Khan、Hélio A. Stefani

  DOI：10.5935/0103-5053.20150038

  日期：——

  We reported a fast and easy method for obtaining biarylic units from tyrosine derivatives via Suzuki-Miyaura cross-coupling using a variety of substituted and unsubstituted potassium aryl-and heteroaryltrifluoroborate salts. The scope of the methodology was also extended to the formation of bis-tyrosine linked dipeptide bonds, leading to biologically interesting compounds. Some biarylic units were obtained as free amino acids through the one step cleavage reaction in good yields.
• Evaluation of toxicity on epithelial and tumor cells of biaryl dipeptide tyrosines
  作者：Stanley N.S. Vasconcelos、Carine C. Drewes、Leonard de Vinci Kanda Kupa、Sandra H.P. Farsky、Hélio A. Stefani

  DOI：10.1016/j.ejmech.2016.02.062

  日期：2016.5

  We report a method to obtain biaryl dipeptide tyrosine via Suzuki-Miyaura and alkynyl dipeptide tyrosine by Sonogashira cross-coupling reactions. Analysis of the biological action of biaryl dipeptide tyrosine 4d compound showed its ability to impair the metabolism and proliferation of SK-Mel-28 human melanoma lineage cells, independently of mitochondrial membrane depolarization, apoptosis and necrosis. Moreover, 4d compound did not cause toxicity to human umbilical vein endothelial cells (HUVEC), suggesting its toxic specificity to cancer cells. (C) 2016 Elsevier Masson SAS. All rights reserved.