1,1-dimethylethyl (2S)-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-pentenoate | 367275-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1,1-dimethylethyl (2S)-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-pentenoate
• 英文别名: tert-butyl (2S)-2-{[(9H-fluoren-9-ylmethoxy)]carbonylamino}-4-pentenoate；(S)-tert-butyl 2-((9H-fluoren-9-yl)methoxycarbonylamino)pent-4-enoate；N-Fmoc-allylglycine tert-butyl ester；tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-enoate
• CAS: 367275-82-9
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: GEOLSZUQALRRMC-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (2S)-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-pentenoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 、 三甲基氢氧化锡 作用下， 以 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 38.0h， 生成 (2S,7S)-8-tert-butoxycarbonyl-2-tert-butoxycarbonylamino-7-((9H-fluoren-9-yl)methoxycarbonylamino)heptanoic acid
  参考文献：
  名称：

  Replacement of the Disulfide Bridge in a KLK3-Stimulating Peptide Using Orthogonally Protected Building Blocks

  摘要：

  Peptide "B-2", which is one of the most potent kallikrein-related peptidase 3 (KLK3)-stimulating compounds, consists of 12 amino acids and is cyclized by a disulfide bridge between the N- and C-terminal cysteines. Orthogonally protected building blocks were used in the peptide synthesis to introduce a disulfide bridge mimetic consisting of four carbon atoms. The resulting pseudopeptides with alkane and E-alkene linkers doubled the proteolytic activity of KLK3 at a concentration of 14 mu M. They were almost as potent as the parent "B-2" peptide, which gives a 3.6-fold increase in the proteolytic activity of KLK3 at the same concentration.

  DOI：

  10.1021/ml400419g
• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 在 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 环己烷 、 水 为溶剂， 生成 1,1-dimethylethyl (2S)-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-pentenoate
  参考文献：
  名称：

  Synthesis of conformationally constrained γ-d-glutamyl-meso-diaminopimelic acid derivatives as ligands of nucleotide-binding oligomerization domain protein 1 (Nod1)

  摘要：

  Nod1, an important member of the pattern recognition receptor family, remains a virtually unexploited target. Harnessing its innate immune stimulatory properties still remains an unfulfilled goal of medicinal chemistry. Nucleotide-binding oligomerization domain protein 1 (Nod1) agonists have been shown to boost the inflammatory responses against pathogenic microbes and could thus constitute a new class of broad spectrum antimicrobial agents. To gain additional insight into the structure/activity relationships of Nod1 agonistic compounds, a series of novel, conformationally constrained gamma-D-glutamyl-meso-diaminopimelic acid (iE-DAP) analogs have been designed and synthesized. Ramos-Blue cells expressing Nod1 were used to screen and validate our compounds for their Nod1-agonist activity. Their immunomodulatory properties were subsequently determined in vitro, by evaluating their capacity to induce proinflammatory cytokine and chemokine production from human peripheral blood mononuclear cells (PBMC), by themselves and in synergy with lipopolysaccharide (LPS), a Toll-like receptor 4 (TLR4) ligand. The synthesized iE-DAP analogs were shown to possess immuno-enhancing properties as a result of their potent and specific Nod1-agonistic effect. The activity of the compound exhibiting the greatest capacity to induce pro-inflammatory cytokine release from PBMC surpassed that of lauroyl-gamma-D-glutamyl-mesodiaminopimelic acid (C12-iE-DAP). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.022

文献信息

• Straightforward Synthesis of Chiral Silylated Amino Acids through Hydrosilylation
  作者：Damien Marchand、Jean Martinez、Florine Cavelier

  DOI：10.1002/ejoc.200800066

  日期：2008.6

  A method using hydrosilylation of unsaturated amino acids was developed and optimised to obtain silylated amino acids. The platinum (Bu4N)2PtCl6 complex was identified as the best catalyst, and the procedure tolerated different unsaturated substrates, silane reagents and protecting groups. Seven silicon-containing α-amino acids were prepared in an enantiomerically pure form under mild conditions in

  开发并优化了使用不饱和氨基酸氢化硅烷化的方法以获得硅烷化氨基酸。铂 (Bu4N)2PtCl6 配合物被认为是最好的催化剂，该过程可以耐受不同的不饱和底物、硅烷试剂和保护基团。七种含硅的 α-氨基酸在温和条件下以良好的收率制备成对映异构纯形式，具有正交保护，可广泛用于肽合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Design of α-<i>S</i>-Neoglycopeptides Derived from MUC1 with a Flexible and Solvent-Exposed Sugar Moiety
  作者：Víctor Rojas-Ocáriz、Ismael Compañón、Carlos Aydillo、Jorge Castro-Loṕez、Jesús Jiménez-Barbero、Ramón Hurtado-Guerrero、Alberto Avenoza、María M. Zurbano、Jesús M. Peregrina、Jesús H. Busto、Francisco Corzana

  DOI：10.1021/acs.joc.6b00833

  日期：2016.7.15

  linker between the carbohydrate (GalNAc) and the peptide backbone. The main conformations of these molecules in solution have been evaluated by combining NMR experiments and molecular dynamics simulations. The linker plays a key role in the modulation of the conformation of these compounds at different levels, blocking a direct contact between the sugar moiety and the backbone, promoting a helix-like conformation

  使用基于MUC1糖肽的疫苗是治疗癌症的有前途的方法。我们在本文中提出了几种并入MUC1序列的磺胺类Tn抗原，它们在碳水化合物（GalNAc）和肽主链之间具有可变的接头。这些分子在溶液中的主要构象已经通过结合NMR实验和分子动力学模拟进行了评估。接头在调节这些化合物在不同水平上的构象，阻止糖部分与骨架之间的直接接触，促进糖基化残基的螺旋状构象并促进糖单元的正确呈递中起关键作用。用于分子识别事件。这些新化合物作为MUC1抗原模拟物的可行性已通过与抗MUC1单克隆抗体复合的这些非天然衍生物之一的X射线衍射结构进行了验证。这些特征以及潜在的缺乏免疫抑制的特性使得这些非天然糖肽成为有希望的候选者，用于设计针对癌症的替代性治疗疫苗。
• Synthesis of Enantiopure Aminocyclopropanes by Diastereoselective Addition of a Chiral Amino Substituted Organozinc Carbenoid to Alkenes
  作者：William B. Motherwell、Guillaume Bégis、Tom D. Sheppard、David E. Cladingboel、Derek A. Tocher

  DOI：10.1055/s-2005-918469

  日期：——

  The synthesis of enantiopure aminocyclopropanes is reported, via direct aminocyclopropanation of alkenes with a zinc carbenoid containing a chiral auxiliary. The methodology was applied to the synthesis of a protected aminocyclopropane present in the immunosuppressant Belactosin A.

  据报道，通过烯烃与含有手性助剂的锌卡宾直接氨基环丙烷化合成对映纯氨基环丙烷。该方法用于合成存在于免疫抑制剂 Belactosin A 中的受保护氨基环丙烷。
• SYNTHESIS OF ALPHA-AMANITIN AND ITS DERIVATIVES
  申请人：Pure Bioorganics SIA

  公开号：EP3792250A1

  公开（公告）日：2021-03-17

  The present invention relates to the chemical synthesis of α-amanitin and its derivatives. The present invention also relates to intermediate products of the α-amanitin synthesis.

  本发明涉及α-amanitin及其衍生物的化学合成。本发明还涉及 α-amanitin 合成的中间产物。
• Synthesis of S-glycosyl amino acids and S-glycopeptides via photoinduced click thiol–ene coupling
  作者：Michele Fiore、Mauro Lo Conte、Salvatore Pacifico、Alberto Marra、Alessandro Dondoni

  DOI：10.1016/j.tetlet.2010.11.097

  日期：2011.1

  We report on the photoinduced addition of glycosyl thiols to alkenyl glycines (thiol-ene coupling) to give S-glycosyl amino acids in high yields (53-90%). One of the amino acids thus prepared was used in the construction of a tripeptide via solution phase chemistry. Moreover, a one-pot two-step approach to an S-glycopeptide was developed using glutathione (GSH) as model starting material. This approach involved GSH S-alkenylation followed by photoinduced hydrothiolation by a glycosyl thiol. (C) 2010 Elsevier Ltd. All rights reserved.