N-Fmoc-N’-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-D-赖氨酸 | 150629-67-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-Fmoc-N’-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-D-赖氨酸
• 中文别名: N-芴甲氧羰基-N'-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-L-赖氨酸；N-FMOC-N'-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-L-赖氨酸；N-芴甲氧羰基-N'-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-D-赖氨酸；N-Fmoc-N'-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-D-赖氨酸；N-Fmoc-N'-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-L-赖氨酸；N-FMOC-N'-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-D-赖氨酸
• 英文名称: Fmoc-L-Lys(Dde)-OH
• 英文别名: Fmoc-Lys(Dde)-OH；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)ethylideneamino]hexanoic acid
• CAS: 150629-67-7
• 化学式: C₃₁H₃₆N₂O₆
• 分子量: 532.637
• InChiKey: AOHSSQNORWQENF-VWLOTQADSA-N

物化性质

• 熔点：
  ~80 °C (dec.)
• 沸点：
  750.1±60.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  2924 29 70
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

制备方法与用途

用途

N-Fmoc-N'-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-D-赖氨是有机合成和医药研发的医药中间体，只作实验室合成研究或者开发之用。

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (1H-imidazole-1-carbonyl)-L-glutamate 、 N-Fmoc-N’-[1-(4,4-二甲基-2,6-二氧代环己亚基)乙基]-D-赖氨酸 、 3-[Ditert-butyl(fluoro)silyl]-5-prop-2-enoxycarbonylbenzoic acid 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以41 %的产率得到
  参考文献：
  名称：

  [EN] SILICON-BASED FLUORIDE ACCEPTOR GROUPS FOR RADIOPHARMACEUTICALS
  [FR] GROUPES ACCEPTEURS DE FLUORURE À BASE DE SILICIUM POUR PRODUITS RADIOPHARMACEUTIQUES

  摘要：

  The invention relates to novel silicon-based fluoride acceptor groups (SiFA groups) of the following formulae (Ia, Ib, Ic) as well as to compounds suitable for use in radiopharmacy comprising such groups, wherein R1and R2are each a linear or branched C3 to C10 alkyl group and R3is selected from (i) -OH or -O-, (ii) a sugar moiety or an amino sugar moiety, (iii) an amino acid moiety or an oligopeptide moiety, (iv) a PEG moiety; and from combinations of two or more of (ii), (iii) and (iv).

  公开号：

  WO2024023332A1

文献信息

• Synthetic Peptides with Genetic‐Codon‐Tailored Affinity for Assembling Tetraspanin CD81 at Cell Interfaces and Inhibiting Cancer Metastasis
  作者：Kun Xu、Han Gao、Yongming Li、Yulong Jin、Rui Zhao、Yanyan Huang

  DOI：10.1002/anie.202400129

  日期：2024.5.13

  Probing biomolecular interactions at cellular interfaces is crucial for understanding and interfering with life processes. Although affinity binders with site specificity for membrane proteins are unparalleled molecular tools, a high demand remains for novel multi‐functional ligands. In this study, a synthetic peptide (APQQ) with tight and specific binding to the untargeted extracellular loop of CD81 evolved from a genetically encoded peptide pool. With tailored affinity, APQQ flexibly accesses, site‐specifically binds, and forms a complex with CD81, enabling in‐situ tracking of the dynamics and activity of this protein in living cells, which has rarely been explored because of the lack of ligands. Furthermore, APQQ triggers the relocalization of CD81 from diffuse to densely clustered at cell junctions and modulates the interplay of membrane proteins at cellular interfaces. Motivated by these, efficient suppression of cancer cell migration, and inhibition of breast cancer metastasis were achieved in vivo.