Fmoc-L-Dap(Boc)-OBn | 668985-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-L-Dap(Boc)-OBn
• 英文别名: benzyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propanoate；Fmoc-Dpr(Boc)-OBn；benzyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 668985-56-6
• 化学式: C₃₀H₃₂N₂O₆
• 分子量: 516.594
• InChiKey: PUJCMWAXKIJSPF-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-L-Dap(Boc)-OBn 在 氨基磺酰氯 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 benzyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(sulfamoylamino)propanoate
  参考文献：
  名称：

  [EN] ANTIBODY DRUG CONJUGATES
  [FR] CONJUGUÉS ANTICORPS-MÉDICAMENT

  摘要：

  Antibody-drug conjugate compounds comprising a linker and methods of using such compounds are provided.

  公开号：

  WO2023125530A1
• 作为产物：
  描述：

  溴甲苯 、 N-Fmoc-N'-Boc-L-2,3-二氨基丙酸 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57.8 %的产率得到Fmoc-L-Dap(Boc)-OBn
  参考文献：
  名称：

  [EN] ANTIBODY DRUG CONJUGATES
  [FR] CONJUGUÉS ANTICORPS-MÉDICAMENT

  摘要：

  Antibody-drug conjugate compounds comprising a linker and methods of using such compounds are provided.

  公开号：

  WO2023125530A1

文献信息

• Lanthanide-binding peptides with two pendant aminodiacetate arms: Impact of the sequence on chelation
  作者：Agnieszka Niedźwiecka、Federico Cisnetti、Colette Lebrun、Christelle Gateau、Pascale Delangle

  DOI：10.1039/c2dt11686c

  日期：——

  Lanthanide complexes with a series of hexapeptides—incorporating two unnatural chelating amino acids with aminodiacetate groups, Ada1 and Ada2—have been examined in terms of their speciation, structure, stability and luminescence properties. Whereas Ada2 acts as a tridentate donor in all cases, Ada1 may act as a tetradentate donor thanks to the coordination of the amide carbonyl function assisted by the formation of a six-membered chelate ring. The position of the Ada1 residue in the sequence is demonstrated to be critical for the lanthanide complex speciation and structure. Ada1 promotes the coordination of the backbone amide function to afford a highly dehydrated Ln complex and an S-shape structure of the peptide backbone, only when found in position 2.

  我们研究了镧系元素与一系列六肽的配合物--其中包含两个带有氨基二乙酸酯基团的非天然螯合氨基酸，即 Ada1 和 Ada2--的配位、结构、稳定性和发光特性。Ada2 在所有情况下都是三叉供体，而 Ada1 则可能是四叉供体，这要归功于酰胺的羰基官能团在形成六元螯合环的帮助下进行配位。事实证明，Ada1 残基在序列中的位置对镧系元素复合物的规格和结构至关重要。只有当 Ada1 位于位置 2 时，才会促进骨架酰胺功能的配位，从而产生高度脱水的 Ln 复合物和肽骨的 S 型结构。
• Alanine Scan of [<scp>l</scp>-Dap²]Ramoplanin A2 Aglycon:  Assessment of the Importance of Each Residue
  作者：Joonwoo Nam、Dongwoo Shin、Yosup Rew、Dale L. Boger

  DOI：10.1021/ja068573k

  日期：2007.7.1

  ramoplanin A2 aglycon, a potent antibiotic that inhibits bacterial cell wall biosynthesis, is detailed. As a consequence of both its increased stability (lactam vs lactone) and its "relative" ease of synthesis, the alanine scan was conducted on [Dap2]ramoplanin A2 aglycon, which possesses antimicrobial activity equal to or slightly more potent than that of ramoplanin A2 or its aglycon. Thus, 14 key

  在定义每个残基的重要性并确定分子的关键区域的工作中，详细介绍了 ramoplanin A2 苷元的丙氨酸扫描，这是一种抑制细菌细胞壁生物合成的强效抗生素。由于其稳定性（内酰胺与内酯）的增加及其“相对”易于合成，对 [Dap2] 雷莫拉宁 A2 苷元进行了丙氨酸扫描，其具有与雷莫拉宁 A2 相同或略强的抗菌活性或其苷元。因此，制备了 ramoplanin A2 苷元的 14 个关键类似物，代表残基 3-13、15 和 17 的扫描，采用收敛的溶液相全合成，将努力巩固到可管理的水平。
• Total Synthesis and Examination of Three Key Analogues of Ramoplanin: A Lipoglycodepsipeptide with Potent Antibiotic Activity
  作者：Yosup Rew、Dongwoo Shin、Inkyu Hwang、Dale L. Boger

  DOI：10.1021/ja039671y

  日期：2004.2.1

  The total synthesis and evaluation of three key ramoplanin aglycon analogues are detailed. The first (5a) represents replacement of the labile depsipeptide ester with a stable amide (HAsn2 --> Dap2) with removal of the HAsn pendant carboxamide, and it was found to be slightly more potent than the natural aglycon in antimicrobial assays providing a new lead structure with an improved profile and a more stable and accessible macrocyclic template on which to conduct structure-function studies. In contrast, a second amide analogue 5b which contains a single additional methylene relative to 5a (HAsn2 --> Dab2) was found to be inactive in antimicrobial assays (>100-fold loss in activity). The third key analogue 5c in which the Asn1 lipid side chain was replaced with an acetyl group revealed that it contributes significantly to the antimicrobial activity (16-fold) of the ramoplanins, but is not essential.
• US8987306B2
  申请人：——

  公开号：US8987306B2

  公开（公告）日：2015-03-24