desthiobiotin azide methyl ester | 1006727-87-2

• 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 methyl ester
• 英文别名: methyl 6-[(4R,5S)-5-(azidomethyl)-2-oxoimidazolidin-4-yl]hexanoate
• CAS: 1006727-87-2
• 化学式: C₁₁H₁₉N₅O₃
• 分子量: 269.304
• InChiKey: DTDFOYWJATZEAB-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-(5'-Methoxycarbonylpentyl)-5-mesyloxymethylimidazolidin-2-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以495 mg的产率得到desthiobiotin azide 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

• Biomolecular Labelling Using Multifunctional Biotin Analogues
  申请人：Thomas Neil R.

  公开号：US20120083599A1

  公开（公告）日：2012-04-05

  Novel biotin analogues, such as 2-Azidobiotin, comprising the ureido ring of natural biotin with the thiophene ring, optionally modified, and a modified sidechain having a functional end group, preferably selected from the group consisting of a carboxylic acid, amine, alcohol, thiol, aldehyde and a halide, and at least one bio-orthogonally reactive chemical group located elsewhere in the sidechain. The analogues are used for labelling target structures and biomolecules, such as peptides and proteins in vitro or in vivo.

  新型生物素类似物，例如2-叠氮基生物素，包括天然生物素的尿素环和噻吩环，可选择性地改性，以及具有功能末端基团的改性侧链，优选从羧酸、胺、醇、硫醇、醛和卤素组成的群中选择，并且在侧链的其他位置至少有一个生物正交反应化学基团。这些类似物用于在体内或体外标记靶结构和生物分子，例如肽和蛋白质。
• [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