N^α-(tert-butoxycarbonyl)-N^ε-[(fluoren-9-ylmethoxy)carbonyl]-L-lysinamide | 98318-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N^α-(tert-butoxycarbonyl)-N^ε-[(fluoren-9-ylmethoxy)carbonyl]-L-lysinamide
• 英文别名: (S)-(9H-fluoren-9-yl)methyl tert-butyl (6-amino-6-oxohexane-1,5-diyl)dicarbamate；Boc-Lys(Fmoc)-NH2；tert-butyl N-[(2S)-1-amino-6-(9H-fluoren-9-ylmethoxycarbonylamino)-1-oxohexan-2-yl]carbamate
• CAS: 98318-02-6
• 化学式: C₂₆H₃₃N₃O₅
• 分子量: 467.565
• InChiKey: HSGXKDQEPBFGMY-QFIPXVFZSA-N

物化性质

• 沸点：
  706.6±60.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-(tert-butoxycarbonyl)-N^ε-[(fluoren-9-ylmethoxy)carbonyl]-L-lysinamide 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N-甲基吡咯烷酮 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Unsaturated acyl chains dramatically enhanced cellular uptake by direct translocation of a minimalist oligo-arginine lipopeptide

  摘要：

  不饱和脂肪酰链有利于短阳离子NBD标记肽的直接转位。

  DOI：

  10.1039/c5cc06116d
• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-[(2,4-dimethoxyphenyl)methylamino]-6-(9H-fluoren-9-ylmethoxycarbonylamino)-1-oxohexan-2-yl]carbamate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以69%的产率得到N^α-(tert-butoxycarbonyl)-N^ε-[(fluoren-9-ylmethoxy)carbonyl]-L-lysinamide
  参考文献：
  名称：

  Selective N-debenzylation of amides with p-TsOH

  摘要：

  N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxyl-benzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02738-7

文献信息

• Synthesis of Peptidoglycan Units with UDP at the Anomeric Position
  作者：Thierry Lioux、Roger Busson、Jef Rozenski、Martine Nguyen-Distèche、Jean-Marie Frère、Piet Herdewijn

  DOI：10.1135/cccc20051615

  日期：——

  A series of UDP-disaccharide peptide compounds were synthesized as synthetic substrate analogues or potential inhibitors of glycosyl transferase. Fluorescent compounds have been prepared with the aim of developing a screening method for selecting transglycosylase inhibitors.

  一系列UDP-二糖肽化合物被合成为糖基转移酶的合成底物类似物或潜在抑制剂。已经制备了荧光化合物，目的是开发一种筛选方法，用于选择转糖基酶抑制剂。
• DIPEPTIDE ANALOGS AS TGF-BETA INHIBITORS
  申请人：SOUTHERN RESEARCH INSTITUTE

  公开号：US20190127420A1

  公开（公告）日：2019-05-02

  The present disclosure is concerned with dipeptide analogs that are capable of inhibiting TGF-β and methods of treating cancers such as, for example, multiple myeloma and a hematologic malignancy, methods for immunotherapy, and methods of treating fibrotic conditions using these compounds. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本公开涉及能够抑制TGF-β的二肽类似物，以及治疗癌症（例如多发性骨髓瘤和血液恶性肿瘤）、免疫疗法和使用这些化合物治疗纤维化病症的方法。本摘要旨在作为在特定领域搜索的扫描工具，并不意味着对本发明的限制。
• Modular Synthesis of DOTA‐Metal‐Based PSMA‐Targeted Imaging Agents for MRI and PET of Prostate Cancer
  作者：Hans F. Schmitthenner、Damien E. Dobson、Kelsea G. Jones、Nnamdi Akporji、Dana Q. M. Soika、Kent L. Nastiuk、Joseph P. Hornak

  DOI：10.1002/chem.201903390

  日期：2019.11.4

  practical, convergent synthesis of prostate-specific membrane antigen (PSMA) targeted imaging agents for MRI, PET, and SPECT of prostate cancer has been developed. In this approach, metals chelated to 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) were placed on the side chains of lysine early in the synthesis to form imaging modules. These are coupled to targeting modules, in this case

  已经开发了实用，收敛的前列腺癌的MRI，PET和SPECT靶向前列腺特异性膜抗原（PSMA）成像剂的合成方法。在这种方法中，在合成初期，将螯合至1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸（DOTA）的金属置于赖氨酸的侧链上，以形成成像模块。它们与靶向模块偶联，在这种情况下，靶向模块由与激活的接头结合的PSMA结合尿素DCL组成。靶向分子成像剂（TMIA）的模块化方法具有明显的优势。通过尽早螯合MRI对比金属Gd，它可以兼作DOTA的保护基。可以利用标准的偶联和脱保护步骤将模块组装成肽，并且避免了需要用强酸除去的DOTA的三叔丁基保护。在最终步骤中，这可以使成像模块与多种靶向剂温和结合。进一步发现，在合成过程中，两种不稳定的金属La3 +或Ce3 +可以用作DOTA中的占位符，然后在弱酸中被PET / SPECT中使用的金属Cu2 +，Ga3 +，In3 +和Y3 +转化。这
• Synthesis and Antagonistic Activity of Two Covalently Linked Dimers of Adrenocorticotropin-(11-24)-tetradecapeptide
  作者：Jean-Luc Fauchère

  DOI：10.1002/hlca.19850680327

  日期：1985.5.15

  The chemical synthesis of two dimers of the sequence 11 to 24 of adrenocorticotropin is described. The two monomers were covalently linked through their N-or C-termini, respectively, using N-acetylglutamic acid or lysine amide as spacers. Compared to the monomer, the first dimer showed moderately, the second strongly increased inhibitory potency upon steroidogenesis in isolated adrenal cells.

  描述了肾上腺皮质激素序列11至24的两个二聚体的化学合成。使用N-乙酰谷氨酸或赖氨酸酰胺作为间隔基，这两个单体分别通过其N-末端或C-末端共价连接。与单体相比，第一个二聚体显示适度，而第二个二聚体在分离的肾上腺细胞中对类固醇生成的抑制能力大大增强。
• Unsaturated acyl chains dramatically enhanced cellular uptake by direct translocation of a minimalist oligo-arginine lipopeptide
  作者：J.-M. Swiecicki、M. Di Pisa、F. Lippi、S. Chwetzoff、C. Mansuy、G. Trugnan、G. Chassaing、S. Lavielle、F. Burlina

  DOI：10.1039/c5cc06116d

  日期：——

  Unsaturated acyl chain favours direct translocation of short cationic NBD-labelled peptide.

  不饱和脂肪酰链有利于短阳离子NBD标记肽的直接转位。