desthiobiotin azide | 1006727-80-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: desthiobiotin azide
• 英文别名: 8-azidodesthiobiotin
• CAS: 1006727-80-5
• 化学式: C₁₀H₁₇N₅O₃
• 分子量: 255.277
• InChiKey: VYUOPFORSNBQLQ-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  127.19
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  desthiobiotin azide methyl ester 在 甲醇 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以70%的产率得到desthiobiotin azide
  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

• [EN] BIOMOLECULAR LABELLING USING MULTIFUNCTIONAL BIOTIN ANALOGUES<br/>[FR] MARQUAGE BIOMOLÉCULAIRE UTILISANT DES ANALOGUES MULTIFONCTIONNELS DE BIOTINE
  申请人：UNIV NOTTINGHAM

  公开号：WO2010106347A8

  公开（公告）日：2011-12-22