N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-4-penten-1-yl-glycine | 227006-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-4-penten-1-yl-glycine
• 英文别名: N-Fmoc-N-(4-penten-1-yl)-glycine；2-[9H-fluoren-9-ylmethoxycarbonyl(pent-4-enyl)amino]acetic acid
• CAS: 227006-56-6
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: VQYFJYJEJACPRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-4-penten-1-yl-glycine 在 N-甲基吗啉 、 Grubbs catalyst first generation 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 {2-[[(E)-6-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-hex-4-enyl]-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-acetylamino}-acetic acid methyl ester
  参考文献：
  名称：

  Cross-metathesis of N-alkenyl peptoids with O- or C-allyl glycosides

  摘要：

  Cross-metathesis of several N-alkenyl-containing oligoglycines derivatives (peptoids) with protected O-or C-allyl glycosides of N-acetylglucosamine, galactose, and mannose using Grubbs' ruthenium benzylidene catalyst (Cy3P)(2)Cl2Ru=CHPh (1) has been achieved in 40 to 52% yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00481-5
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 N-(4-pentenyl)glycine methyl ester 在 水 、 sodium hydroxide 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-4-penten-1-yl-glycine
  参考文献：
  名称：

  Application of ring-closing metathesis macrocyclization to the development of Tsg101-binding antagonists

  摘要：

  HIV-1 viral budding involves binding of the viral Gag(p6) protein to the ubiquitin E2 variant domain of the human tumor susceptibility gene 101 protein (Tsg101). Recognition of p6 by Tsg101 is mediated in part by a proline-rich motif that contains the sequence 'Pro-Thr-Ala-Pro' ('PTAP'). Using the p6-derived 9-mer sequence 'PEPTAPPEE', we had previously improved peptide binding affinity by employing N-alkylglycine ('peptoid') residues. The current study applies ring-closing metathesis macrocyclization strategies to Tsg101-binding peptide-peptoid hybrids as an approach to stabilize binding conformations and to observe the effects of such macrocyclization on Tsg101-binding affinity and bioavailability. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.10.105