Fmoc-Lys(DOTA-OH)-OH | 1611478-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Lys(DOTA-OH)-OH
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetyl]amino]hexanoic acid
• CAS: 1611478-62-6
• 化学式: C₃₇H₅₀N₆O₁₁
• 分子量: 754.838
• InChiKey: YAIUTDOWWMVABL-HKBQPEDESA-N

物化性质

• 沸点：
  1040.1±65.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7.3
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  230
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  terbium(III) chloride 、 Fmoc-Lys(DOTA-OH)-OH 在 盐酸 、 ammonium acetate 作用下， 以 水 、 乙腈 为溶剂， 以73%的产率得到
  参考文献：
  名称：

  Solid Phase Synthesis of Short Peptide-Based Multimetal Tags for Biomolecule Labeling

  摘要：

  We describe an unprecedented solid phase peptide synthesis (SPPS) of short peptide-based multimetal tags designated as elemental tags for the quantification of biomolecules via inductively coupled plasma mass spectrometry (ICP-MS). The macrocyclic chelator 1,4,7,10-tetraazacyclododecane N,N',N″,N‴-tetra acetic acid (DOTA) was attached to the side chain of N-α-(9-fluorenylmethoxycarbonyl)-l-lysine (Fmoc-Lys-OH) and metalated with a lanthanide to provide a building block for Fmoc-based SPPS. Thereby, in contrast to existing strategies for the synthesis of DOTA-peptide conjugates, an already metalated DOTA-amino acid was used as a building block for SPPS. The DOTA-lanthanide complex was stable throughout the whole SPPS, even during the final cleavage in concentrated trifluoroacetic acid. This indicates that the strategy to first metalate the Fmoc-Lys(DOTA)-OH and to utilize the metal coordination to protect the carboxyl groups of DOTA offers an alternative to conventional synthetic routes using tert-butyl protected DOTA. Several small peptides containing up to four metal ions were synthesized, among them peptides carrying defined metal sequences consisting of two different lanthanides. The peptides were N-terminally maleimide-functionalized, thus introducing a moiety for conjugation to thiol-bearing biomolecules. The final objective of this work was the signal enhancement in ICP-MS-based DNA quantification assays. To evaluate the performance of the multimetal peptide tags in assay, they were applied to label thiol-modified 15mer DNA oligonucleotide probes. These served as reporter probes in a model sandwich-type hybridization assay. Thereby, we found that the ICP-MS signal increased linearly with the number of lanthanide ions attached to the reporter probe.

  DOI：

  10.1021/bc500082k
• 作为产物：
  描述：

  (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(2-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)hexanoic acid 在 水 、 三氟乙酸 作用下， 反应 3.5h， 以90.3%的产率得到Fmoc-Lys(DOTA-OH)-OH
  参考文献：
  名称：

  Modular Imaging Agents Containing Amino Acids and Peptides

  摘要：

  靶向药物是由耦合在一起的成像氨基酸或成型的多模式、多螯合金属、多染料成像剂所衍生的，或者这些的组合，可以直接共轭，或者被激活，或者附着到连接剂上，连接剂上可以连接靶向基团，如肽、蛋白质、抗体、寡核苷酸或小分子抑制剂，在合成的最后步骤中共轭，形成各种各样的TMIAs。

  公开号：

  US20150038672A1