(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethyldisulfanyl}-ethyl)-carbamic acid tert-butyl ester | 1190626-67-5

• 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: (2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethyldisulfanyl}-ethyl)-carbamic acid tert-butyl ester
• CAS: 1190626-67-5
• 化学式: C₁₉H₃₄N₄O₄S₃
• 分子量: 478.701
• InChiKey: PLVDSZPBZKVBQN-DZKIICNBSA-N

物化性质

• 熔点：
  112.6 °C
• 沸点：
  760.0±60.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  108.56
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethyldisulfanyl}-ethyl)-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoic acid [2-(2-amino-ethyldisulfanyl)-ethyl]-amide hydrochloride salt
  参考文献：
  名称：

  Fluorometric assay for tissue transglutaminase-mediated transamidation activity

  摘要：

  Herein, we report the development of a direct discontinuous fluorometric transamidation assay for determining tissue transglutaminase (TG2) activity. In the assay reaction, TG2 catalyzes the formation of a biotin-fluorophore conjugate, using a fluorescent, high affinity gamma-glutamyl donor substrate and a biotinylated amine as a gamma-glutamyl acceptor substrate. After the reaction, the conjugate is fixed on streptavidin-coated beads and excess substrate is washed away, allowing the transamidation activity to be quantified by fluorescence measurement. This method was used to detect the activity of as little as 0.6 mU of purified TG2, and can be used for detection of activity from crude cellular lysates. Furthermore, this assay can be used for screening potential inhibitors and synthetic substrates, the latter of which was demonstrated herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.031
• 作为产物：
  描述：

  D-生物素 、 T-BOC-胱胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以54%的产率得到(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethyldisulfanyl}-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Fluorometric assay for tissue transglutaminase-mediated transamidation activity

  摘要：

  Herein, we report the development of a direct discontinuous fluorometric transamidation assay for determining tissue transglutaminase (TG2) activity. In the assay reaction, TG2 catalyzes the formation of a biotin-fluorophore conjugate, using a fluorescent, high affinity gamma-glutamyl donor substrate and a biotinylated amine as a gamma-glutamyl acceptor substrate. After the reaction, the conjugate is fixed on streptavidin-coated beads and excess substrate is washed away, allowing the transamidation activity to be quantified by fluorescence measurement. This method was used to detect the activity of as little as 0.6 mU of purified TG2, and can be used for detection of activity from crude cellular lysates. Furthermore, this assay can be used for screening potential inhibitors and synthetic substrates, the latter of which was demonstrated herein. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.031

文献信息

• Spatiotemporal Investigation of Intercellular Heterogeneity via Multiple Photocaged Probes
  作者：Chun‐Yi Tsai、Po‐Hsun Chen、Ai‐Lin Chen、Tsung‐Shing Andrew Wang

  DOI：10.1002/chem.202301067

  日期：2023.9.15

  Intercellular heterogeneity occurs widely under both normal physiological environments and abnormal disease‐causing conditions. Several attempts to couple spatiotemporal information to cell states in a microenvironment were performed to decipher the cause and effect of heterogeneity. Furthermore, spatiotemporal manipulation can be achieved with the use of photocaged/photoactivatable molecules. Here, we provide a platform to spatiotemporally analyze differential protein expression in neighboring cells by multiple photocaged probes coupled with homemade photomasks. We successfully established intercellular heterogeneity (photoactivable ROS trigger) and mapped the targets (directly ROS‐affected cells) and bystanders (surrounding cells), which were further characterized by total proteomic and cysteinomic analysis. Different protein profiles were shown between bystanders and target cells in both total proteome and cysteinome. Our strategy should expand the toolkit of spatiotemporal mapping for elucidating intercellular heterogeneity.

  摘要 在正常生理环境和异常致病条件下，细胞间异质性广泛存在。为了破译异质性的原因和影响，人们多次尝试将时空信息与微环境中的细胞状态结合起来。此外，利用光笼/可光电激活的分子可以实现时空操纵。在这里，我们提供了一个平台，通过多个光笼式探针和自制光掩膜，对相邻细胞中不同的蛋白质表达进行时空分析。我们成功地建立了细胞间异质性（可光激活的 ROS 触发器），并绘制了目标（直接受 ROS 影响的细胞）和旁观者（周围的细胞）的图谱。在总蛋白组和半胱氨酸组中，旁观者细胞和目标细胞的蛋白质特征各不相同。我们的策略应能扩展时空图谱工具包，用于阐明细胞间的异质性。