penilumamide B

• 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: penilumamide B
• 英文别名: methyl (S)-2-(2-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropteridine-6-carboxamido)-4-(methylthio)butanamido)benzoate；Penilumamide B；methyl 2-[[(2S)-2-[(1,3-dimethyl-2,4-dioxopteridine-6-carbonyl)amino]-4-methylsulfanylbutanoyl]amino]benzoate
• 化学式: C₂₂H₂₄N₆O₆S
• 分子量: 500.535
• InChiKey: BOEKMUKDDSBLKQ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  penilumamide B 在 Oxone 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以75%的产率得到penilumamide C
  参考文献：
  名称：

  A straight forward and first total synthesis of Penilumamides B–D

  摘要：

  A simple and straight forward first total synthesis of rare lumazine peptides, Penilumamide B, C and D isolated from the marine-derived fungi Aspergillus and Penicillium sp. is described from a common starting material, 1,3-dimethyllumazine-6-carboxylic acid. Penilumamide C was prepared from Penilumamide B by oxidation of the methionine residue to the corresponding sulphone. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.07.027
• 作为产物：
  描述：

  1,3-dimethyllumazine-6-carboxylic acid 在 水 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.5h， 生成 penilumamide B
  参考文献：
  名称：

  A straight forward and first total synthesis of Penilumamides B–D

  摘要：

  A simple and straight forward first total synthesis of rare lumazine peptides, Penilumamide B, C and D isolated from the marine-derived fungi Aspergillus and Penicillium sp. is described from a common starting material, 1,3-dimethyllumazine-6-carboxylic acid. Penilumamide C was prepared from Penilumamide B by oxidation of the methionine residue to the corresponding sulphone. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.07.027

文献信息

• A versatile strategy for the synthesis of various lumazine peptides
  作者：Wanli Zhang、Andrew R. Mahoney、Michelle Garrison、William M. Wuest

  DOI：10.1007/s00044-023-03097-9

  日期：2023.7

  ubiquitous and serves as a significant bio-precursor in living cells. Additionally, it can be found in multiple natural products that exhibit intriguing activities. We report here a versatile and straightforward total synthesis of a series of lumazine peptides. Fluorescence titration experiments validate the metal binding characteristics of the synthesized compounds to Fe (III) and weak to no affinities

  Lumazine 是一种含氮杂环化合物，无处不在，是活细胞中重要的生物前体。此外，它还存在于多种具有有趣活性的天然产品中。我们在这里报告了一系列 lumazine 肽的通用且直接的全合成。荧光滴定实验验证了合成化合物与 Fe (III) 的金属结合特性以及与 Cu (II)、Co (II) 和 Mn (II) 的弱亲和力或无亲和力。 图形概要
• A straight forward and first total synthesis of Penilumamides B–D
  作者：Thirupathi Reddy Penjarla、Maheshwar Kundarapu、Baquer Syed Mohd.、Anupam Bhattacharya

  DOI：10.1016/j.tetlet.2017.07.027

  日期：2017.8

  A simple and straight forward first total synthesis of rare lumazine peptides, Penilumamide B, C and D isolated from the marine-derived fungi Aspergillus and Penicillium sp. is described from a common starting material, 1,3-dimethyllumazine-6-carboxylic acid. Penilumamide C was prepared from Penilumamide B by oxidation of the methionine residue to the corresponding sulphone. (C) 2017 Elsevier Ltd. All rights reserved.