Boc-Arg(NO2^G)-Osu | 60526-35-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-Arg(NO2^G)-Osu
• 英文别名: N^α-Boc-N^ω-nitro-L-arginine N-hydroxysuccinimide ester；Boc-Arg(NO2)-ONSu；Boc-Arg(NO2)-OSu；(2,5-dioxopyrrolidin-1-yl) (2S)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 60526-35-4
• 化学式: C₁₅H₂₄N₆O₈
• 分子量: 416.391
• InChiKey: CNHOKOAQPTUOAD-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  198
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-Arg(NO2^G)-Osu 在 palladium on activated charcoal 吡啶 、 TEA 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 生成 thymopentin
  参考文献：
  名称：

  Becu, Fr.; Becu, Chr.; Anteunis, M. J. O., Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 1, p. 15 - 23

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Boc-N'-硝基-L-精氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 Boc-Arg(NO2^G)-Osu
  参考文献：
  名称：

  Becu, Fr.; Becu, Chr.; Anteunis, M. J. O., Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 1, p. 15 - 23

  摘要：

  DOI：

文献信息

• Artificial ribonucleases 6. Ribonuclease activity of tetrapeptides based on amino acids involved in the catalytic site of RNase T1
  作者：L. S. Koroleva、A. A. Donina、N. V. Tamkovich、N. A. Kovalev、M. A. Zenkova、V. N. Sil’nikov

  DOI：10.1007/s11172-006-0176-4

  日期：2005.11

  Tetrapeptides based on amino acids involved in the catalytic site of RNase T1 were synthesized. These peptides interact with a 96-mer fragment of HIV-1 RNA, which results in phosphodiester bonds splitting. The efficacy of RNA cleavage depends on the mutual arrangement of oppositely charged amino acids (Glu and Arg or Lys) in a peptide. The introduction of an additional cationic fragment (based on bis-quaternary salts of 1,4-diazabicyclooctane) into an RNase mimetic leads to a considerable increase in the efficiency of RNA depolymerization.

  基于RNase T1催化位点氨基酸的四肽已被合成。这些肽与HIV-1 RNA的96-mer片段相互作用，导致磷酸二酯键断裂。RNA切割的效力取决于相反电荷氨基酸（Glu和Arg或Lys）在肽中的相互排列。将附加的阳离子片段（基于1,4-二氮杂双环[4.2.0]辛烷的双季铵盐）引入模拟RNase的结构中，显著提高了RNA解聚的效率。
• Improving the synthesis of hemin derivatives and their effect on bacterial biofilms
  作者：Sergey V. Blagodarov、Galina A. Zheltukhina、Yuliya M. Romanova、Natalia V. Alekseeva、Lyudmila D. Iskhakova、Maria I. Semashko、Eteri R. Tolordava、Vladimir E. Nebolsin

  DOI：10.1142/s1088424622500079

  日期：2022.3

  The emergence of antibiotic-resistant bacterial strains has recently resulted in a large focus on designing new antimicrobial agents, including those based on natural compounds. We have previously synthesized two disubstituted arginine-containing derivatives of hemin (HD) (4) and (5) that demonstrated pronounced antimicrobial activity against planktonic cells in vitro [1, 2]. These HDs are leading and promising for the creation of antibacterial agents on their basis. This research is aimed at improving the synthesis of HDs (4) and (5) to increase their yield, simplify the process and minimize the side reactions, as well as to establish their antimicrobial and destructive effect on biofilms, including those consisting of antibiotic-resistant bacteria. As a result, we were able to increase the yields of the protected dipeptide of ZArg(Z[Formula: see text]SerNH₂ (3) and the corresponding HD (4) up to 97 and 93%, respectively, and also to minimize the side reaction of the formation of ornithine-containing HD. For the arginine amide modified HD (5), we have also proposed an improved synthesis scheme. The ability of HD to cause the bacteria death in the composition of formed biofilms, including those consisting of resistant bacteria, was shown. After the effect of HDs on the biofilm at concentrations of 80 and 100 [Formula: see text]g/ml, the CFU decrease was 3–5/ml. The fluorescent microscopy confirmed the bacteria mortality in the biofilm. Electron microscopy showed structural damage (fragmentation) of the formed bacterial biofilm under the effect of HDs.

  抗生素耐药菌株的出现导致人们最近开始关注设计新的抗菌剂，包括基于天然化合物的抗菌剂。我们之前合成了两种含精氨酸的二取代海明（HD）衍生物 (4) 和 (5)，它们在体外对浮游细胞具有明显的抗菌活性 [1，2]。这些 HD 是在其基础上制造抗菌剂的主要原料，前景广阔。这项研究的目的是改进 HDs (4) 和 (5) 的合成，以提高它们的产量、简化过程并尽量减少副反应，同时确定它们对生物膜（包括由抗生素耐药菌组成的生物膜）的抗菌和破坏作用。因此，我们能够将受保护的 ZArg(Z[式：见正文]SerNH2(3))二肽和相应的 HD(4)的产量分别提高到 97% 和 93%，并将形成含鸟氨酸 HD 的副反应降至最低。对于精氨酸酰胺修饰的 HD（5），我们也提出了一种改进的合成方案。结果表明，在已形成的生物膜（包括由抗性细菌组成的生物膜）中，HD 能够导致细菌死亡。浓度为 80 和 100 [式中：见正文]克/毫升的 HD 对生物膜产生作用后，CFU 的减少量为 3-5/毫升。荧光显微镜证实了生物膜中细菌的死亡。电子显微镜显示，在 HDs 的作用下，已形成的细菌生物膜结构受损（破碎）。
• Design, RNA cleavage and antiviral activity of new artificial ribonucleases derived from mono-, di- and tripeptides connected by linkers of different hydrophobicity
  作者：Nikolay Tamkovich、Lyudmila Koroleva、Mikhail Kovpak、Elena Goncharova、Vladimir Silnikov、Valentin Vlassov、Marina Zenkova

  DOI：10.1016/j.bmc.2016.02.007

  日期：2016.3

  A novel series of metal-free artificial ribonucleases (aRNases) was designed, synthesized and assessed in terms of ribonuclease activity and ability to inactivate influenza virus WSN/A33/H1N1 in vitro. The compounds were built of two short peptide fragments, which include Lys, Ser, Arg, Glu and imidazole residues in various combinations, connected by linkers of different hydrophobicity (1,12-diaminododecane

  根据核糖核酸酶活性和体外灭活流感病毒WSN / A33 / H1N1的能力，设计，合成和评估了一系列新型的无金属人工核糖核酸酶（aRNase）。这些化合物由两个短肽片段组成，包括不同组合的Lys，Ser，Arg，Glu和咪唑残基，并通过不同疏水性的接头（1,12-二氨基十二烷或4,9-dioxa-1,12-二氨基十二烷）连接）。这些化合物在生理条件下有效裂解不同的RNA底物，其速率比上述人工核糖核酸酶高三到五倍，并显示出类似RNase A的裂解特异性。具有疏水性1,12-二氨基十二烷接头的aRNase的核糖核酸酶活性比具有4,9-dioxa-1,12-二氨基十二烷接头的aRNase高3–40倍。假定的RNA裂解机制是天然核糖核酸酶的典型机制，即通过aRNase中存在的氨基酸的官能团形成酸/碱对形成一般的酸碱催化作用。裂解的pH曲线证实了这一机理。在生理条件下短暂的病毒悬浮培养后，研究中最活
• β-Lactam Derivatives as Enzyme Inhibitors: Carboxy Peptidyl Derivatives of (S)-4-Oxoazetidine-2-carboxylate as Peptidomimetics
  作者：Martin Schneider、Hans-Hartwig Otto

  DOI：10.1002/1521-4184(200105)334:5<167::aid-ardp167>3.3.co;2-f

  日期：2001.5

  4-Oxoazetidine-2-carboxylic acid, protected at the nitrogen by silyl groups, was coupled with amino acid and oligopeptide esters. Desilylation and deprotection of the amino acid residues yielded the free beta -lactam peptides. Structure and properties were elucidated by spectroscopic methods and discussed. Some selected compounds were tested as fibrinogen inhibitors and for thrombocyte aggregation. None of the compounds showed any activity up to a concentration of 10(-5) Mol/l. Some other compounds exhibited a weak inhibitory activity against elastase (PPE).
• Artificial ribonucleases. 5. Synthesis and ribonuclease activity of tripeptides composed of amino acids involved in catalytic centers of natural ribonucleases
  作者：I. L. Kuznetsova、N. S. Zhdan、M. A. Zenkova、V. V. Vlassov、V. N. Sil"nikov

  DOI：10.1023/b:rucb.0000030824.26304.cb

  日期：2004.2