N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-3-buten-1-yl-glycine | 227006-55-5

• 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-3-buten-1-yl-glycine
• 英文别名: N-Fmoc-N-(3-buten-1-yl)-glycine；2-[but-3-enyl(9H-fluoren-9-ylmethoxycarbonyl)amino]acetic acid
• CAS: 227006-55-5
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: IJBPAHPUQGXDLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  甘胺酸甲酯 、 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-3-buten-1-yl-glycine 在 N-甲基吗啉 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以98%的产率得到{2-[But-3-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：

  氯甲酸-9-芴基甲酯 、 homoallylglycine 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-3-buten-1-yl-glycine
  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

文献信息

• A thiol–ene mediated approach for peptide bioconjugation using ‘green’ solvents under continuous flow
  作者：Inés Rabadán González、Joshua T. McLean、Nikita Ostrovitsa、Sheila Fitzgerald、Andrea Mezzetta、Lorenzo Guazzelli、Donal F. O'Shea、Eoin M. Scanlan

  DOI：10.1039/d4ob00122b

  日期：——

  Flow chemistry has emerged as an integral process within the chemical sector permitting energy efficient synthetic scale-up while improving safety and minimising solvent usage. Herein, we report the first applications of the photoactivated, radical-mediated thiol–ene reaction for peptide bioconjugation under continuous flow. Bioconjugation reactions employing deep eutectic solvents, bio-based solvents

  流动化学已成为化学领域的一个不可或缺的过程，可以实现节能合成规模扩大，同时提高安全性并最大限度地减少溶剂使用。在此，我们报告了光活化、自由基介导的硫醇-烯反应在连续流下肽生物共轭中的首次应用。本文报道了使用低共熔溶剂、生物基溶剂和全水系统进行的一系列生物相关肽底物的生物共轭反应。使用水溶性光引发剂 Irgacure 2959 可以在完全水性条件下合成糖基化肽，无需添加有机溶剂，并增强了这些快速光活化生物共轭反应的绿色资质。
• Application of ring-closing metathesis macrocyclization to the development of Tsg101-binding antagonists
  作者：Fa Liu、Andrew G. Stephen、Abdul A. Waheed、Eric O. Freed、Robert J. Fisher、Terrence R. Burke

  DOI：10.1016/j.bmcl.2009.10.105

  日期：2010.1

  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.