5-((3aS)-2,5ξ-dioxo-(3ar,6ac)-octahydro-5λ⁴-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester | 215095-81-1

• 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: 5-((3aS)-2,5ξ-dioxo-(3ar,6ac)-octahydro-5λ⁴-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester
• 英文别名: methyl 5-[(3aS,4S,6aR)-2,5-dioxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate
• CAS: 215095-81-1
• 化学式: C₁₁H₁₈N₂O₄S
• 分子量: 274.341
• InChiKey: DUQYHVINYNWYEU-MTYDSQGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-((3aS)-2,5ξ-dioxo-(3ar,6ac)-octahydro-5λ⁴-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester 在 三氟乙酸酐 、 水 作用下， 以 氯仿 、 四氢呋喃 为溶剂， 以21%的产率得到C₁₁H₁₈N₂O₅S
  参考文献：
  名称：

  Expanding the Substrate Tolerance of Biotin Ligase through Exploration of Enzymes from Diverse Species

  摘要：

  Technologies that enable the site-specific conjugation of chemical probes onto proteins are extremely useful for applications in cell biology and proteomics. We cloned, expressed, and purified biotin ligases from nine different species and screened them for the ability to ligate unnatural analogues of biotin onto the human p67 biotin acceptor domain. We discovered that the biotin ligases of Saccharomyces cerevisiae (yeast) and Pyrococcus horikoshii could accept alkyne and azide derivatives of biotin, respectively. HPLC, gel-shift, and mass spectrometry assays confirmed that these ligation reactions were ATP-and enzyme-dependent, as well as site-specific. We used the P. horikoshii-catalyzed azide ligation reaction to site-specifically introduce a phosphine probe onto p67 using the Staudinger ligation. These new ligation reactions demonstrate the differential substrate specificities of biotin ligases from different organisms and open the door to novel protein labeling applications.

  DOI：

  10.1021/ja076655i
• 作为产物：
  描述：

  D-生物素甲酯 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 生成 5-((3aS)-2,5ξ-dioxo-(3ar,6ac)-octahydro-5λ⁴-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester
  参考文献：
  名称：

  Expanding the Substrate Tolerance of Biotin Ligase through Exploration of Enzymes from Diverse Species

  摘要：

  Technologies that enable the site-specific conjugation of chemical probes onto proteins are extremely useful for applications in cell biology and proteomics. We cloned, expressed, and purified biotin ligases from nine different species and screened them for the ability to ligate unnatural analogues of biotin onto the human p67 biotin acceptor domain. We discovered that the biotin ligases of Saccharomyces cerevisiae (yeast) and Pyrococcus horikoshii could accept alkyne and azide derivatives of biotin, respectively. HPLC, gel-shift, and mass spectrometry assays confirmed that these ligation reactions were ATP-and enzyme-dependent, as well as site-specific. We used the P. horikoshii-catalyzed azide ligation reaction to site-specifically introduce a phosphine probe onto p67 using the Staudinger ligation. These new ligation reactions demonstrate the differential substrate specificities of biotin ligases from different organisms and open the door to novel protein labeling applications.

  DOI：

  10.1021/ja076655i

文献信息

• Biotin as a Reactive Handle to Selectively Label Proteins and DNA with Small Molecules
  作者：Adam D. Cotton、James A. Wells、Ian B. Seiple

  DOI：10.1021/acschembio.1c00252

  日期：2022.12.16

  (BioReACT), expands the utility of biotin labeling and enables a predictable and stable chemical conjugation to biomolecules without the need to screen for a suitable methionine conjugation site. We demonstrate the versatility of this approach by producing a fluorescently labeled antibody, an antibody–drug conjugate, and a small molecule-conjugated oligonucleotide. We anticipate that BioReACT will be useful

  生物素是与蛋白质和 DNA 生物偶联的常见功能手柄，但其用途仅限于含蛋白质的偶联配偶体，例如链霉亲和素及其衍生物。最近，开发了氧氮丙啶试剂，可选择性地将蛋氨酸的硫醚偶联到蛋白质表面，这种方法称为氧化还原激活化学标记 (ReACT)。这些试剂生成的硫酰亚胺键的稳定性取决于溶剂的可及性和 oxaziridine 上的取代。在这里，我们表明氧氮丙啶试剂与生物素中的硫醚快速反应，生成在 37 °C 下可稳定超过 10 天的亚硫酰亚胺产物。这种方法，我们称之为生物素氧化还原激活化学标记 (BioReACT)，扩展了生物素标记的实用性，并实现了与生物分子的可预测和稳定的化学缀合，而无需筛选合适的甲硫氨酸缀合位点。我们通过生产荧光标记抗体、抗体-药物偶联物和小分子偶联寡核苷酸证明了这种方法的多功能性。我们预计 BioReACT 将有助于使用生物素将双正交手柄快速引入生物分子，生物素是一种广泛存在且易于安装的官能团。
• NOVEL BIOTIN-SPECIFIC MONOCLONAL ANTIBODY AND USE THEREOF
  申请人：Roche Diagnostics Operations, Inc.

  公开号：US20190324025A1

  公开（公告）日：2019-10-24

  The present invention relates to a monoclonal antibody capable of binding to biotin. In one embodiment the monoclonal antibody according to the invention also does not bind to a biotin moiety on a biotinylated molecule, wherein the biotin moiety is attached to the molecule via the carbon atom of the carboxyl function of the valeric acid moiety of biotin. Also disclosed is a method for generation of an antibody as disclosed herein. The monoclonal antibody according to the invention is of specific use in a method for measuring an analyte in a sample, wherein a (strept)avidin/biotin pair is used to bind a biotinylated analyte specific binding agent to a (strept)avidin coated solid phase.