tert-butyl (5-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)pentyl)carbamate | 328273-17-2

• 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
• 英文名称: tert-butyl (5-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)pentyl)carbamate
• 英文别名: t-butyl 5-biotinamidopentylcarbamate；tert-butyl N-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentyl]carbamate
• CAS: 328273-17-2
• 化学式: C₂₀H₃₆N₄O₄S
• 分子量: 428.596
• InChiKey: QKFLRHKHYLQHHC-ZOBUZTSGSA-N

物化性质

• 沸点：
  714.3±55.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (5-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)pentyl)carbamate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-(5-biotinamidopentyl)okadaamide
  参考文献：
  名称：

  Development of Biotin–Avidin Technology to Investigate Okadaic Acid-Promoted Cell Signaling Pathway

  摘要：

  Four biotin conjugates of okadaic acid were synthesized for evaluating their interactions with protein phosphatase 2A (PP2A) by surface plasmon resonance (SPR). C7-biotinylated okadaic acid exhibited the strongest binding affinity to the enzyme, while Cl-biotinylated derivative was devoid of affinity. C24- or C27-biotinylated okadaic acid showed moderate affinity to the enzyme. In the wake of this finding, a biotinyl photoaffinity probe was introduced into 7-OH of okadaic acid. Photoaffinity labeling followed by SDS-PAGE analysis indicated that the okadaic acid derivative clearly labeled PP2A. Furthermore, three proteins were also labeled in crude extracts of a marine sponge Halichondria okadai. All these results imply that the C7-biotin conjugate is a versatile reagent for biochemical studies of okadaic acid-binding proteins including PP2A. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00752-3
• 作为产物：
  描述：

  N-(5-氨基戊基)氨基甲酸叔丁酯 、 D-生物素 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到tert-butyl (5-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)pentyl)carbamate
  参考文献：
  名称：

  设计，合成，抗肿瘤活性和新型二芳基取代的稠合杂环作为针对微管蛋白和katanin的双重配体的生物学研究

  摘要：

  微管是治疗癌症的重要靶标之一。基于结合原理，通过结合β-内酰胺和嘌呤类化合物的结构，设计了一类新型的二芳基取代的咪唑并[4,5-c]吡啶-2-酮和咪唑并[4,5-c]吡啶。微管蛋白聚合抑制剂和katanin活性上调剂分别。在体外评估了它们的抗肿瘤活性并阐明了其机制，从而鉴定出1,6-二芳基-1 H-咪唑并[4,5-c]吡啶2-2（3 H）-one 20b作为第一种双功能剂可以同时靶向微管蛋白和katanin。在体内测定证实化合物20b的 具有良好的药代动力学特征，可显着抑制异种移植肿瘤的生长，这表明它具有进一步发展成为具有双重靶向微管独特机制的抗肿瘤药物候选物的潜力。

  DOI：

  10.1016/j.ejmech.2019.05.072

文献信息

• [EN] BIOPROBES FOR LYSYL OXIDASES AND USES THEREOF<br/>[FR] BIOSONDES POUR LYSYL OXYDASES ET LEURS UTILISATIONS
  申请人：PHARMAXIS LTD

  公开号：WO2021155439A1

  公开（公告）日：2021-08-12

  The present invention relates to novel bioprobes which are capable of binding to certain amine oxidase enzymes. These bioprobes are useful in methods of detecting and determining the concentration of certain amine oxidase enzymes in a sample as well as in methods for the quantitative assessment of inhibition of certain amine oxidases.

  本发明涉及能够结合特定胺氧化酶的新型生物探针。这些生物探针在检测和确定样本中特定胺氧化酶的浓度的方法中是有用的，同时也可用于定量评估特定胺氧化酶的抑制方法。
• [EN] PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS<br/>[FR] PROFILAGE DE PHOTOPROXIMITÉ D'INTERACTIONS PROTÉINE-PROTÉINE DANS DES CELLULES
  申请人：UNIV CHICAGO

  公开号：WO2021055960A1

  公开（公告）日：2021-03-25

  Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.

  描述了用于检测生物相互作用的光活性探针和探针系统。光活性探针包括同时结合光解和光反应基团的探针。光活性探针系统可以包括第一探针，其中包括光催化基团，以及第二探针，其中包括可作为光催化基团催化反应底物的基团。探针和探针系统还可以包括能够特异性结合到感兴趣生物实体上的结合伙伴的基团，以及可检测的基团或其前体。这些探针和探针系统可以检测蛋白质或细胞的时空相互作用。在某些实施方式中，这些相互作用可以在活细胞中检测到。还描述了检测生物相互作用的方法。
• Rational Development of Novel Activity Probes for the Analysis of Human Cytochromes P450
  作者：Jonathan D. Sellars、Mark Skipsey、Sadr-ul-Shaheed、Sebastian Gravell、Hamza Abumansour、Ghasaq Kashtl、Jawaria Irfan、Mohamed Khot、Klaus Pors、Laurence H. Patterson、Chris W. Sutton

  DOI：10.1002/cmdc.201600134

  日期：2016.6.6

  (CYPs) in biological samples is proving important for robust analyses of drug efficacy and metabolic disposition. In this study, a novel CYP activity-based probe was rationally designed and synthesised, demonstrating selective binding of CYP isoforms. The dependence of probe binding upon the presence of NADPH permits the selective detection of functionally active CYP. This allows the detection and analysis

  事实证明，生物样品中功能性细胞色素P450（CYP）的鉴定和定量对于药物功效和代谢处置的可靠分析非常重要。在这项研究中，合理设计和合成了一种新型的基于CYP活性的探针，证明了CYP亚型的选择性结合。探针结合对NADPH的存在的依赖性允许选择性检测功能活性CYP。这允许使用生化和蛋白质组学方法论和方法对这些酶进行检测和分析。
• An improved synthesis of a fluorophosphonate–polyethylene glycol–biotin probe and its use against competitive substrates
  作者：Hao Xu、Hairat Sabit、Gordon L Amidon、H D Hollis Showalter

  DOI：10.3762/bjoc.9.12

  日期：——

  markedly increases the efficiency of the probe synthesis and overcomes several problems of a prior synthesis. As a proof of principle, FP-PEG-biotin was evaluated against isolated protein mixtures and different rat-tissue homogenates, showing its ability to specifically target serine hydrolases. We also assessed the ability of FP-PEG-biotin to compete with substrates that have high enzyme turnover rates. The

  连接到生物素标签的氟膦酸盐 (FP) 部分是一种原型化学探针，用于通过称为基于活性的蛋白质分析 (ABPP) 的方法定量分析和富集复杂蛋白质组中的活性丝氨酸水解酶。在这项研究中，我们设计了一种新的合成路线，以通过聚乙二醇将已知的 FP 探针连接到生物素标签 (FP-PEG-生物素)。我们的路线显着提高了探针合成的效率并克服了先前合成的几个问题。作为原理证明，针对分离的蛋白质混合物和不同的大鼠组织匀浆对 FP-PEG-生物素进行了评估，显示了其特异性靶向丝氨酸水解酶的能力。我们还评估了 FP-PEG-生物素与具有高酶周转率的底物竞争的能力。
• NOVEL OPTICAL LABELING MOLECULES FOR PROTEOMICS AND OTHER BIOLOGICAL ANALYSES
  申请人：DRATZ Edward

  公开号：US20100252433A1

  公开（公告）日：2010-10-07

  The invention relates to compositions and methods useful in the labeling and identification of changes in protein levels, changes in enzyme activity, and changes in protein modification. The invention provides for highly soluble optical labeling molecules which are optionally cleavable after separation of mixtures of labeled proteins into components. These optical labeling molecules find utility in a variety of applications, including use in the field of proteomics.

  本发明涉及用于标记和识别蛋白质水平变化、酶活性变化和蛋白质修饰变化的组合物和方法。本发明提供了高度溶解的光学标记分子，这些分子在将标记蛋白质的混合物分离成组分后可选择性地被裂解。这些光学标记分子在各种应用中具有实用性，包括在蛋白质组学领域的应用。