生物素酰基-4-氨基丁酸 | 35924-87-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 中文名称: 生物素酰基-4-氨基丁酸
• 英文名称: 4-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)butanoic acid
• 英文别名: 4-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]butanoic acid
• CAS: 35924-87-9
• 化学式: C₁₄H₂₃N₃O₄S
• 分子量: 329.42
• InChiKey: DDXWHXMZPONLDF-KWBADKCTSA-N

物化性质

• 沸点：
  728.4±55.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  生物素酰基-4-氨基丁酸 在 氯化亚砜 、 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  用于探测Nur77蛋白诱导途径的生物素化强心苷的设计与合成。

  摘要：

  孤儿核受体Nur77（也称为TR3或神经生长因子诱导的克隆B NGFI-B）在调节靶基因表达中起核转录因子的作用，并且在分化，增殖，凋亡，和许多不同细胞类型的存活率 最近的研究表明，Nur77还涉及许多重要的生理和病理过程，包括癌症，炎症和免疫力，心血管疾病和骨骼疾病。我们以前的研究表明强心苷可以诱导Nur77蛋白的表达及其从细胞核到细胞质的转运，然后靶向线粒体，从而导致癌细胞凋亡。为了探测Nur77蛋白的诱导途径，我们设计并合成了一系列新型的生物素化的强心苷，它们分别来自β-安提香和α-安提香，这是两种来自安提阿里斯毒株的典型强心苷。评价了这些生物素化强心苷Nur77蛋白表达的诱导及其对NIH-H460癌细胞增殖的抑制作用。结果表明，一些生物素化的强心苷可以显着诱导Nur77蛋白的表达，与它们的母体化合物β-Antiarin和α-Antiarin相当。而且，评估了它们的抗生蛋白链菌素结合

  DOI：

  10.1016/j.bmcl.2019.01.015
• 作为产物：
  描述：

  tert-butyl 4-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)butanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 生物素酰基-4-氨基丁酸
  参考文献：
  名称：

  Target-Specific Chemical Acylation of Lectins by Ligand-Tethered DMAP Catalysts

  摘要：

  Because sugar-binding proteins, so-called lectins, play important roles in many biological phenomena, the lectin-selective labeling should be useful for investigating biological processes involving lectins as well as providing molecular tools for analysis of saccharides and these derivatives. We describe herein a new strategy for lectin-selective labeling based on an acyl transfer reaction directed by ligand-tethered DIVIAP (4-dimethylaminopyridine). DIVIAP is an effective acyl transfer catalyst, which can activate an acyl ester for its transfer to a nucleophilic residue. To direct the acyl transfer reaction to a lectin of interest, we attached the DIVIAP to a saccharide ligand specific for the target lectin. It was clearly demonstrated by biochemical analyses that the target-selective labeling of Congerin II, an animal lectin having selective affinity for Lactose/LacNAc (N-acetyllactosamine), was achieved in the presence of Lac-tethered DMAPs and acyl donors containing probes such as fluorescent molecules or biotin. Conventional peptide mapping experiments using HPLC and tandem mass-mass analysis revealed that the acyl transfer reaction site-specifically occurred at Tyr 51 of Cong II. This strategy was successfully extended to other lectins by changing the ligand part of the ligand-tethered DMAP. We also demonstrated that this labeling method is applicable not only to purified lectin in test tubes, but also to crude mixtures such as E coli lysates or homogenized animal tissue samples expressing Congerin.

  DOI：

  10.1021/ja075684q

文献信息

• Artificial Metalloproteins Containing Co₄O₄ Cubane Active Sites
  作者：Lisa Olshansky、Raúl Huerta-Lavorie、Andy I. Nguyen、Jaicy Vallapurackal、Ariel Furst、T. Don Tilley、A. S. Borovik

  DOI：10.1021/jacs.7b13052

  日期：2018.2.28

  Artificial metalloproteins (ArMs) containing Co4O4 cubane active sites were constructed via biotin-streptavidin technology. Stabilized by hydrogen bonds (H-bonds), terminal and cofacial CoIII-OH2 moieties are observed crystallographically in a series of immobilized cubane sites. Solution electrochemistry provided correlations of oxidation potential and pH. For variants containing Ser and Phe adjacent to the

  通过生物素-链霉亲和素技术构建了含有 Co4O4 立方烷活性位点的人工金属蛋白 (ArMs)。通过氢键（H 键）稳定，在一系列固定的立方烷位点通过晶体学观察到末端和共面 CoIII-OH2 部分。溶液电化学提供了氧化电位和 pH 值的相关性。对于含有与金属辅因子相邻的 Ser 和 Phe 的变体，1e-/1H+ 化学占主导地位，直到 pH 值为 8，高于该值时，氧化变得不依赖于 pH 值。在 Co4O4 活性位点附近安装 Tyr 为一组共面 CoIII-OH2 基团中的一个提供了单个 H 键。使用这种变体，观察到多 e-/多 H+ 化学，以及在 pH 9.5 时与 Tyr 去质子化一致的机制变化。
• Design and synthesis of a novel photoaffinity probe for labelling EGF receptor tyrosine kinases
  作者：You-Guang Zheng、Xiao-Qing Wu、Jun Su、Ping Jiang、Liang Xu、Jian Gao、Bin Cai、Min Ji

  DOI：10.1080/14756366.2017.1344979

  日期：2017.1.1

  is one useful approach for the functional analysis of proteins. In this study, a novel photoaffinity probe 11 was designed and synthesised to assess the target profiling of the reactive group in the photoaffinity probe 11. Biological evaluation was performed, and the results showed that the novel photoaffinity probe binds to EGFR and HER2 proteins and it hits targets by the reactive group.

  表皮生长因子受体（EGFR）和HER2是两个重要的酪氨酸激酶，在调节多种细胞功能（包括增殖，分化，迁移和血管生成）的信号转导途径中起着至关重要的作用。在过去的20年中，许多蛋白质组学方法已经成为评估蛋白质在生物过程和人类疾病状态中的有力方法。其中，基于活性的蛋白质谱分析（ABPP）是蛋白质功能分析的一种有用方法。在这项研究中，设计并合成了一种新型光亲和探针11，以评估光亲和探针11中反应基团的靶图谱。进行了生物学评估，结果表明该新型光亲和探针与EGFR和HER2蛋白结合，达到反应小组的目标。
• [EN] SUBSTITUTED HETEROARYL COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSÉS HÉTÉROARYLE SUBSTITUÉS ET LEUR UTILISATION
  申请人：HELIOS HUAMING BIOPHARMA CO LTD

  公开号：WO2022078294A1

  公开（公告）日：2022-04-21

  The present disclosure provides substituted heteroaryl compounds and use thereof, also provides compounds or pharmaceutically acceptable salts or solvates thereof as PAD inhibitors and their use in treatment of a disease or disorder.

  本公开提供了取代的杂环芳香化合物及其用途，还提供了作为PAD抑制剂的化合物或其药学上可接受的盐或溶剂，并将其用于治疗疾病或障碍。
• Artificial Metalloenzymes:  (Strept)avidin as Host for Enantioselective Hydrogenation by Achiral Biotinylated Rhodium−Diphosphine Complexes
  作者：Myriem Skander、Nicolas Humbert、Jérôme Collot、Julieta Gradinaru、Gérard Klein、Andreas Loosli、Jérôme Sauser、Andrea Zocchi、François Gilardoni、Thomas R. Ward

  DOI：10.1021/ja0476718

  日期：2004.11.1

  We report on the generation of artificial metalloenzymes based on the noncovalent incorporation of biotinylated rhodium-diphosphine complexes in (strept)avidin as host proteins. A chemogenetic optimization procedure allows one to optimize the enantioselectivity for the reduction of acetamidoacrylic acid (up to 96% ee (R) in streptavidin S112G and up to 80% ee (S) in WT avidin). The association constant between a prototypical cationic biotinylated rhodium-diphosphine catalyst precursor and the host proteins was determined at neutral pH: log K-a = 7.7 for avidin (pl = 10.4) and log K-a = 7.1 for streptavidin (pl = 6.4). It is shown that the optimal operating conditions for the enantioselective reduction are 5 bar at 30 degreesC with a 1% catalyst loading.
• Verfahren zur Bestimmung von HIV-Antikörpern
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0379949B1

  公开（公告）日：1995-03-29