FMOC-S-3-氨基-5-己炔酸 | 1217669-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-S-3-氨基-5-己炔酸
• 英文名称: (S)-3-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}hex-5-ynoic acid
• 英文别名: Fmoc-L-β-homopropargylglycine；Fmoc-L-β³-Pra-OH；(S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hex-5-ynoic acid；(3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)hex-5-ynoic acid
• CAS: 1217669-02-7
• 化学式: C₂₁H₁₉NO₄
• 分子量: 349.386
• InChiKey: ALHPEVGGGAQSCG-AWEZNQCLSA-N

物化性质

• 沸点：
  591.5±50.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  FMOC-S-3-氨基-5-己炔酸 、 L-缬氨酸甲酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到(S)-methyl 2-{(S)-3-[(((9H-fluoren-9-yl)methoxy)carbonyl)amino]hex-5-ynamido}-3-methylbutanoate
  参考文献：
  名称：

  Azide- and Alkyne-Functionalised α- and β3-Amino Acids

  摘要：

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.

  DOI：

  10.1055/s-0032-1317445
• 作为产物：
  描述：

  Fmoc-L-炔丙基甘氨酸 在 N-甲基吗啉 、 silver trifluoroacetate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 生成 FMOC-S-3-氨基-5-己炔酸
  参考文献：
  名称：

  Azide- and Alkyne-Functionalised α- and β3-Amino Acids

  摘要：

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.

  DOI：

  10.1055/s-0032-1317445

文献信息

• EGF Receptor-Targeting Peptide Conjugate Incorporating a Near-IR Fluorescent Dye and a Novel 1,4,7-Triazacyclononane-Based ⁶⁴Cu(II) Chelator Assembled via Click Chemistry
  作者：Katrin Viehweger、Lisa Barbaro、Karina Pombo García、Tanmaya Joshi、Gerhard Geipel、Jörg Steinbach、Holger Stephan、Leone Spiccia、Bim Graham

  DOI：10.1021/bc5001388

  日期：2014.5.21

  A new Boc-protected 1,4,7-triazacyclononane (TACN)-based pro-chelator compound featuring a "clickable" azidomethylpyridine pendant has been developed as a building block for the construction of multimodal imaging agents. Conjugation to a model alkyne (propargyl alcohol), followed by deprotection, generates a pentadentate ligand, as confirmed by X-ray crystallographic analysis of the corresponding distorted square-pyramidal Cu(II) complex. The ligand exhibits rapid Cu-64(II)-binding kinetics (>95% radiochemical yield in <5 min) and a high resistance to demetalation. It may thus prove suitable for use in Cu-64(II)-based in vivo positron emission tomography (PET). The new chelating building block has been applied to the construction of a bimodal (PET/fluorescence) peptide-based imaging probe targeting the epidermal growth factor (EGF) receptor, which is highly overexpressed on the surface of several types of cancer cells. The probe consists of a hexapeptide sequence, Leu-Ala-Arg-Leu-Leu-Thr (designated "D4"), followed by a Cys-beta-Ala-beta-Ala spacer, then a beta-homopropargylglycine residue with the TACN-based chelator "clicked" to its side chain. A sulfonated near-infrared (NIR) fluorescent cyanine dye (sulfo-Cy5) was introduced at the N-terminus to study the EGF receptor-binding ability of the probe by laser-fluorescence spectroscopy. Binding was also confirmed by coimmunoprecipitation methods, and an apparent dissociation constant (K-d) of ca. 10 nM was determined from radioactivity-based measurements of probe binding to two EGF receptor-expressing cell lines (FaDu and A431). The probe is shown to be a biased or partial allosteric agonist of the EGF receptor, inducing phosphorylation of Thr669 and Tyr992, but not the Tyr845, Tyr998, Tyr1045, Tyr1068, or Tyr1148 residues of the receptor, in the absence of the orthosteric EGF ligand. Additionally, the probe was found to suppress the EGF-stimulated autophosphorylation of these latter residues, indicating that it is also a noncompetitive antagonist.
• Azide- and Alkyne-Functionalised α- and β3-Amino Acids
  作者：Daniel Pedersen、Tjerk Sminia

  DOI：10.1055/s-0032-1317445

  日期：——

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.