4-(5'-Methoxycarbonylpentyl)-5-mesyloxymethylimidazolidin-2-one | 1006727-86-1

• 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: 4-(5'-Methoxycarbonylpentyl)-5-mesyloxymethylimidazolidin-2-one
• 英文别名: 6-(5-methanesulfonyloxymethyl-2-oxo-imidazolidin-4-yl)hexanoic acid methyl ester；methyl 6-[(4R,5R)-5-(methylsulfonyloxymethyl)-2-oxoimidazolidin-4-yl]hexanoate
• CAS: 1006727-86-1
• 化学式: C₁₂H₂₂N₂O₆S
• 分子量: 322.382
• InChiKey: NXDLAOPMDVXQBN-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  6-((4R,5R)-5-Hydroxymethyl-2-oxo-imidazolidin-4-yl)-hexanal 在 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 4-(5'-Methoxycarbonylpentyl)-5-mesyloxymethylimidazolidin-2-one
  参考文献：
  名称：

  Even, L.; Florentin, D.; Marquet, A., Bulletin de la Societe Chimique de France, 1990, # 6, p. 758 - 768

  摘要：

  DOI：

文献信息

• Biotin biosynthesis: synthesis and biological evaluation of the putative intermediate thiols
  作者：Andree Marquet、Francois Frappier、Georges Guillerm、Michel Azoulay、Dominique Florentin、Jean Claude Tabet

  DOI：10.1021/ja00059a006

  日期：1993.3

  biotin biosynthesis, the sulfuur insertion into dethiobiotin should involve a thiol as intermediate. The three possible thiols have been synthesized and their biological activity was evaluated: the primary thiol 10 labeled with [ 35 S] or [ 34 S] or with deuterium was transformed into biotin by resting cells of Bacillus sphaericus without loss of the label. Hence, it is a possible intermediate. Interestingly

  先前的结果得出的结论是，生物素生物合成的最后一步，硫插入脱硫生物素应该涉及作为中间体的硫醇。已经合成了三种可能的硫醇并评估了它们的生物活性：用 [ 35 S] 或 [ 34 S] 或用氘标记的初级硫醇 10 被球形芽孢杆菌的静息细胞转化为生物素，而不会丢失标记。因此，它是一个可能的中间体。有趣的是，生长中的细胞将 [ 35 S]- 或 5-[ 2 H 2 ]-标记的 10 转化为生物素，但标记丢失
• [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
• EVEN, L.;FLORENTIN, D.;MARQUET, A., BULL. SOC. CHIM. FR.,(1990) N, C. 758-768
  作者：EVEN, L.、FLORENTIN, D.、MARQUET, A.

  DOI：——

  日期：——