N6-[芴甲氧羰基]-N2-[(2-丙烯基氧基)羰基]-L-赖氨酸 | 186350-56-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N6-[芴甲氧羰基]-N2-[(2-丙烯基氧基)羰基]-L-赖氨酸
• 英文名称: Alloc-Lys(Fmoc)-OH
• 英文别名: Alloc-L-Lys(Fmoc)-OH；(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(prop-2-enoxycarbonylamino)hexanoic acid
• CAS: 186350-56-1
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: SVGIXLCPDFRQJL-QFIPXVFZSA-N

物化性质

• 沸点：
  689.7±55.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P305+P351+P338,P261,P342+P311
• 危险性描述：
  H319,H315,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  N6-[芴甲氧羰基]-N2-[(2-丙烯基氧基)羰基]-L-赖氨酸 在 Rink amide resin 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Biotin Ergopeptide Probes for Dopamine Receptors

  摘要：

  The incorporation of chemical modifications into the structure of bioactive compounds is often difficult because the biological properties of the new molecules must be retained with respect to the native ligand. Ergopeptides, with their high affinities at D-1 and D-2 dopamine receptors, are particularly complex examples. Here, we report the systematic derivatization of two ergopeptides with different peptide-based spacers and their evaluation by radioligand binding assays. Selected spacer-containing ergopeptides with minimal biological alteration and a proper anchoring point were further derivatized with a biotin reporter. Detailed characterization studies identified 13 as a biotin ergopeptide maintaining high affinity and agonist behavior at dopamine receptors, being a useful tool for the study of heteromers involving D1R, D2R, or D3R.

  DOI：

  10.1021/jm101566d
• 作为产物：
  描述：

  N'-Fmoc-L-赖氨酸 、 氯甲酸烯丙酯 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以95%的产率得到N6-[芴甲氧羰基]-N2-[(2-丙烯基氧基)羰基]-L-赖氨酸
  参考文献：
  名称：

  A convenient access to α V β 3 /α V β 5 integrin ligand conjugates: regioselective solid-phase functionalisation of an RGD based peptide

  摘要：

  The cyclopeptide (-RGDfK-) is a potent and selective alpha (V)beta (3)/alpha (V)beta (5) integrin ligand. A methodology for the conjugation of cyclo(-RGDfK-) through the regioselective derivatisation of lysine side chains, either in solution or directly on the solid support, is described. This provides a rapid and flexible chemical entry to conjugated integrin ligands bearing reporter groups for biological investigations or reactive chemical functions for the preparation of new vector systems. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00293-3

文献信息

• Modular Total Synthesis of Farnesyl Analogues of Cell Wall Precursors Lipid I and II Containing the <i>Staphylococcus aureus</i> Pentaglycine Bridge Modification
  作者：Lukas M. Wingen、Marvin Rausch、Tanja Schneider、Dirk Menche

  DOI：10.1021/acs.joc.0c01004

  日期：2020.8.7

  A scalable and modular total synthesis of 3-lipid I and 3-lipid II was accomplished by a novel route involving an efficient solid phase synthesis of the peptide fragment and an effective chemoenzymatic attachment of the second sugar moiety. The generality of this route was further documented by the synthesis of an analogue bearing the pentaglycine interpeptidic bridge modification characteristic for

  通过一种新颖的途径完成了3-脂质I和3-脂质II的可扩展和模块化的总合成，该途径包括肽片段的有效固相合成和第二糖部分的有效化学酶连接。这条路线的普遍性进一步通过合成具有人类病原体金黄色葡萄球菌的五甘氨酸肽间桥修饰特征的类似物来证明。
• Peptide-Based Probes with an Artificial Anion-Binding Motif for Direct Fluorescence “Switch-On” Detection of Nucleic Acid in Cells
  作者：Debabrata Maity、Marija Matković、Shang Li、Martin Ehlers、Junchen Wu、Ivo Piantanida、Carsten Schmuck

  DOI：10.1002/chem.201703813

  日期：2017.12.6

  reports two new peptide‐based fluorescence probes (1 and 2) for the detection of ds‐DNA at physiological pH. Probes 1 and 2 contain a fluorophore, either amino‐naphthalimide or diethyl‐aminocoumarin, respectively, and two identical peptide arms each equipped with a guanidiniocarbonylpyrrole (GCP) anion‐binding motif. These probes show “switch‐on” fluorescence response upon binding to ds‐DNA, whereby

  这项工作报告了两种新的基于肽的荧光探针（1和2），用于在生理pH下检测ds-DNA。探针1和2分别含有一个荧光团，即氨基萘二甲酰亚胺或二乙基氨基香豆素，以及两个相同的肽臂，每个肽臂都带有一个胍基羰基吡咯（GCP）阴离子结合基序。这些探针在与ds-DNA结合后显示“开启”荧光响应，从而可以区分各种类型的多核苷酸。例如，与富含GC的多核苷酸相比，它们对富含AT的多核苷酸表现出更明显的荧光反应，而对ds-RNA的响应却微不足道。1的荧光响应与DNA中AT碱基对的含量成正比，而2的荧光对多核苷酸的二级结构敏感。荧光实验，热解链实验和圆二色性研究表明，1与ds-DNA相互作用的结合是插入和小沟结合，而2则主要与DNA / RNA的外表面相互作用。由于1和2的细胞毒性非常低，因此1可以用于细胞核DNA的成像。
• [EN] METHYLGLYOXAL-SCAVENGING CYCLIC PEPTIDES AND THEIR USE FOR THE PREVENTION AND TREATMENT OF DISEASES ASSOCIATED WITH ELEVATED METHYLGLYOXAL LEVELS<br/>[FR] PEPTIDES CYCLIQUES PIÉGEURS DE MÉTHYLGLYOXAL ET LEUR UTILISATION POUR LA PRÉVENTION ET LE TRAITEMENT DE MALADIES ASSOCIÉES À DES TAUX ÉLEVÉS DE MÉTHYLGLYOXAL
  申请人：RUPRECHT KARLS UNIV

  公开号：WO2018087028A1

  公开（公告）日：2018-05-17

  The present invention relates to cyclic peptide compounds which inhibit or antagonize the binding of methylglyoxal (MG) and/or other reactive carbonyl species (RCS) to an arginine-or lysine- containing protein. Preferred scavenger compounds are said cyclic peptides comprising a specific amino acid motif and a hydrophobic modification, and pharmaceutical compositions thereof. The present invention furthermore relates to the use of the cyclic peptides as scavenger or antagonists of methylglyoxal and/or related reactive carbonyl species (RCS). The present invention furthermore relates to the use of the cyclic peptides for the prevention and/or treatment of a disease caused by or associated with methylglyoxal (MG) and/or reactive carbonyl species (RCS), in particular caused by or associated with elevated MG levels, such as diabetes and its associated complications, cardiovascular diseases and obesity.

  本发明涉及环肽化合物，其抑制或拮抗甲基乙二醛（MG）和/或其他反应性酮基物（RCS）与含精氨酸或赖氨酸的蛋白质结合。首选清除剂化合物为具有特定氨基酸基序列和疏水修饰的环肽，以及其制备的药物组合物。本发明还涉及将环肽用作甲基乙二醛和/或相关反应性酮基物（RCS）的清除剂或拮抗剂。本发明还涉及将环肽用于预防和/或治疗由甲基乙二醛（MG）和/或反应性酮基物（RCS）引起或相关的疾病，特别是由升高的MG水平引起或相关的糖尿病及其相关并发症、心血管疾病和肥胖症等。
• “Clickable” Albumin Binders for Modulating the Tumor Uptake of Targeted Radiopharmaceuticals
  作者：Florian Brandt、Martin Ullrich、Markus Laube、Klaus Kopka、Michael Bachmann、Reik Löser、Jens Pietzsch、Hans-Jürgen Pietzsch、Jörg van den Hoff、Robert Wodtke

  DOI：10.1021/acs.jmedchem.1c01791

  日期：2022.1.13
• CYTOTOXIC COMPOUNDS
  申请人：[en]PHEON THERAPEUTICS LTD

  公开号：WO2024127332A1

  公开（公告）日：2024-06-20

  The present disclosure provides, inter alia, glycosylated compounds and conjugates thereof useful for treating cancer.