(9H-fluoren-9-yl)methyl (S)-1-azido-3-methylpentan-2-ylcarbamate | 391624-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl (S)-1-azido-3-methylpentan-2-ylcarbamate
• 英文别名: Fmoc-Ile-ψ[CH2N3]；9H-fluoren-9-ylmethyl N-[(2S,3S)-1-azido-3-methylpentan-2-yl]carbamate
• CAS: 391624-30-9
• 化学式: C₂₁H₂₄N₄O₂
• 分子量: 364.447
• InChiKey: TTZKNHMWYUKXSM-VBKZILBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (S)-1-azido-3-methylpentan-2-ylcarbamate 在 氯仿 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以87%的产率得到(9H-fluoren-9-yl)methyl (S)-1-amino-3-methylpentan-2-ylcarbamate hydrochloride
  参考文献：
  名称：

  N-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides

  摘要：

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).

  DOI：

  10.1021/jo900675s
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl ((2S,3S)-1-iodo-3-methylpentan-2-yl)carbamate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以86%的产率得到(9H-fluoren-9-yl)methyl (S)-1-azido-3-methylpentan-2-ylcarbamate
  参考文献：
  名称：

  N-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides

  摘要：

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).

  DOI：

  10.1021/jo900675s

文献信息

• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• Peptidotriazoles with antimicrobial activity against bacterial and fungal plant pathogens
  作者：Imma Güell、Lluís Micaló、Laura Cano、Esther Badosa、Rafael Ferre、Emilio Montesinos、Eduard Bardají、Lidia Feliu、Marta Planas

  DOI：10.1016/j.peptides.2011.12.003

  日期：2012.1

  We designed and prepared peptidotriazoles based on the antimicrobial peptide BP100 (LysLysLeuPheLysLysIleLeuLysTyrLeu-NH2) by introducing a triazole ring in the peptide backbone or onto the side chain of a selected residue. These compounds were screened for their in vitro growth inhibition of bacterial and fungal phytopathogens, and for their cytotoxic effects on eukaryotic cells and tobacco leaves. Their proteolytic susceptibility was also analyzed. The antibacterial activity and the hemolysis were influenced by the amino acid that was modified with the triazole as well as by the absence of presence of a substituent in this heterocyclic ring. We identified sequences active against the bacteria Xanthomonas axonopodis pv. vesicatoria, Erwinia amylovora, Pseudomonas syringae pv. syringae (MIC of 1.6-12.5 mu M), and against the fungi Fusarium oxysporum (MIC < 6.2-12.5 mu M) with low hemolytic activity (0-23% at 50 mu M), high stability to protease digestion and no phytotoxicity. These peptidotriazoles constitute good candidates to design new antimicrobial agents. (C) 2011 Elsevier Inc. All rights reserved.