N,N'-bis(tert-butoxycarbonyl)-6-guanidinylcaproic acid | 158478-79-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N'-bis(tert-butoxycarbonyl)-6-guanidinylcaproic acid
• 英文别名: 6-(2,3-bis(tert-butoxycarbonyl)guanidino)hexanoic acid；6-[2,3-Bis(tert-butoxycarbonyl)guanidino]hexanoic acid；6-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]hexanoic acid
• CAS: 158478-79-6
• 化学式: C₁₇H₃₁N₃O₆
• 分子量: 373.45
• InChiKey: SJUBEIUCRUAHTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N'-bis(tert-butoxycarbonyl)-6-guanidinylcaproic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 6-[6-(N,N′-di-tert-butoxycarbonylguanidino)hexanoylamino]hexanoic acid
  参考文献：
  名称：

  Expansion of Antibacterial Spectrum of Muraymycins toward Pseudomonas aeruginosa

  摘要：

  It is urgent to develop novel anti-Pseudomonas agents that should also be active against multidrug resistant P. aeruginosa. Expanding the antibacterial spectrum of muraymycins toward P. aeruginosa was investigated by the systematic structure activity relationship study. It was revealed that two functional groups, a lipophilic side chain and a guanidino group, at the accessory moiety of muraymycins were important for the anti-Pseudomonas activity, and analogue 29 exhibited antibacterial activity against a range of P. aeruginosa strains with the minimum inhibitory concentration values of 4-8 mu g/mL.

  DOI：

  10.1021/ml5000096
• 作为产物：
  描述：

  6-氨基己酸 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 20.0~100.0 ℃ 、275.79 kPa 条件下， 反应 41.0h， 生成 N,N'-bis(tert-butoxycarbonyl)-6-guanidinylcaproic acid
  参考文献：
  名称：

  Synthesis and evaluation of RGD peptidomimetics aimed at surface bioderivatization of polymer substrates

  摘要：

  Several RGD peptidomimetics have been prepared, in a convergent way, from the common ortho-amino-tyrosine template (O-substituted with an anchorage-arm or a methyl group, and alpha N-substituted with a fluorine tag for XPS analysis), and various omega-aminoacid derivatives. The most flexible compounds have shown a biological activity similar to that of the peptide reference (RGDS) in the platelet aggregation test. The compound 16a could be fitted (by modelisation) with DMP 728 and c(RGDfV), two cyclic peptides that are good ligands of integrins. The compound 16b has been covalently fixed on the surface of a poly(ethylene terephthalate) membrane used as support for mammalian cell cultivation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00083-2

文献信息

• A Convenient Preparation of Monosubstituted<i>N</i>,<i>N</i>′-di(Boc)-Protected Guanidines
  作者：Brian Drake、Marcel Patek、Michal Lebl

  DOI：10.1055/s-1994-25527

  日期：——

  1-H-Pyrazole-1-[N,N′-bis(tert-butoxycarbonyl)] carboxamidine (1) reacts under mild conditions with a number of amines and amino acids to give the respective protected guanidines in moderate to high isolated yields.

  1-H 吡唑-1-[N,N′-双（叔丁氧羰基）]羧酰胺（1）在温和的条件下与多种胺和氨基酸反应，生成相应的受保护胍类化合物，分离产率从中等到高等不等。
• Concise synthesis of spergualin-inspired molecules with broad-spectrum antibiotic activity
  作者：Victoria A. Assimon、Hao Shao、Sylvie Garneau-Tsodikova、Jason E. Gestwicki

  DOI：10.1039/c4md00572d

  日期：——

  There is a growing need to identify new, broad-spectrum antibiotics. The natural productspergualin was previously shown to have promising anti-bacterial activity and a privileged structure, but its challenging synthesis had limited further exploration. For example, syntheses of spergualin and its analogs have been reported in approximately 10 linear steps, with overall yields between 0.3 and 18%. Using

  越来越需要鉴定新的广谱抗生素。先前已证明天然产物pergualin具有令人鼓舞的抗菌活性和特权结构，但其具有挑战性的合成方法限制了其进一步的开发。例如，已经报道了大约10个线性步骤中精子精及其类似物的合成，总收率在0.3％至18％之间。使用Ugi多组分反应，我们只需一步即可组装受精子激发的分子，从而显着提高了总收率（20％至96％）。使用这种策略，我们生成了43种新的类似物，并测试了它们对两种革兰氏阴性和四种革兰氏阳性菌株的抗菌活性。我们发现最有效的类似物化合物6的MIC值为4至32μgmL -1对抗这六种菌株，这对精子蛋白（MIC〜6.25至50μgmL -1）有显着改善。这些研究为使用新型化学支架制备广谱抗生素提供了一条简洁的途径。
• Dynamic Amino Acid Side‐Chains Grafting on Folded Peptide Backbone**
  作者：Benjamin Zagiel、Taleen Peker、Rodrigue Marquant、Guillaume Cazals、Gabrielle Webb、Emeric Miclet、Claudia Bich、Emmanuelle Sachon、Roba Moumné

  DOI：10.1002/chem.202200454

  日期：2022.6.27

  An efficient access to large libraries of conformationally defined peptides is reported, using dynamic combinatorial chemistry as a tool to graft amino acid's side-chains in defined arrangement on a well-ordered 3D peptide scaffold. We report here the design of a chemical system that ensures the scrambling of side-chains on a pre-organized scaffold leading to an isoenergetic library useful for ligand

  据报道，使用动态组合化学作为工具，在有序的 3D 肽支架上以定义的排列方式移植氨基酸的侧链，从而有效地访问大型构象定义的肽库。我们在此报告了一种化学系统的设计，该系统可确保在预先组织的支架上对侧链进行加扰，从而产生可用于配体筛选的等能文库。
• MOLECULAR TRANSPORTERS BASED ON SUGAR AND ITS ANALOGUES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：Chung Sung-Kee

  公开号：US20100330608A1

  公开（公告）日：2010-12-30

  The inventive molecular transporter compound shows significantly high permeability through a biological membrane such as a plasma membrane, nuclear membrane and blood-brain barrier, and accordingly, can be effectively used in delivering various biologically active molecules.

  这种创新的分子转运化合物在生物膜中，如细胞膜、核膜和血脑屏障中，显示出显著的高渗透性，因此可以有效地用于传递各种生物活性分子。
• NG-Acyl-argininamides as NPY Y1 receptor antagonists: Influence of structurally diverse acyl substituents on stability and affinity
  作者：Stefan Weiss、Max Keller、Günther Bernhardt、Armin Buschauer、Burkhard König

  DOI：10.1016/j.bmc.2010.07.028

  日期：2010.9

  N-G-Acylated argininamides, covering a broad range of lipophilicity (calculated log D values: -1.8-12.5), were synthesized and investigated for NPY Y-1 receptor (Y1R) antagonism, Y1R affinity and stability in buffer (N-G-deacylation, yielding BIBP 3226). Broad structural variation of substituents was tolerated. The K-i (binding) and K-b values (Y1R antagonism) varied from low nM to one-digit mu M. Most of the compounds proved to be sufficiently stable at pH 7.4 over 90 min to determine reliable pharmacological data in vitro. Exceptionally high instability was detected when a succinyl moiety was attached to the guanidine, probably, due to an intramolecular cleavage mechanism. (C) 2010 Elsevier Ltd. All rights reserved.