| 1003921-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1003921-93-4
• 化学式: C₁₄H₁₇N₅O₈
• 分子量: 383.318
• InChiKey: IICLSJJNRNRGJH-DKTYCGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  200.15
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 2-acetamido-2-deoxy-5-fluoro-β-D-glucopyranosyl fluoride 、 NagZ from Vibrio cholerae 作用下， 以 various solvent(s) 为溶剂， 生成 2-azidoacetamido-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and Use of Mechanism-Based Protein-Profiling Probes for Retaining β-d-Glucosaminidases Facilitate Identification of Pseudomonas aeruginosa NagZ

  摘要：

  The NagZ class of retaining exo-glucosaminidases play a critical role in pepticloglycan recycling in Gram-negative bacteria and the induction of resistance to beta-lactams. Here we describe the concise synthesis of 2-azidoacetyl-2-deoxy-5-fluoro-beta-D-glucopyranosyl fluoride as an activity-based proteomics probe for profiling these exo-glycosidases. This active-site directed reagent covalently inactivates this class of retaining N-acetylglucosaminidases with exquisite selectivity by stabilizing the glycosyl-enzyme intermediate. Inactivated Vibrio cholerae NagZ can be elaborated with biotin or a FLAG-peptide epitope using the Staudinger ligation or the Sharpless-Meldal click reaction and detected at nanogram levels. This ABPP enabled the profiling of the Pseudomonas aeruginosa proteome and identification at endogenous levels of a tagged protein with properties consistent with those of PA3005. Cloning of the gene encoding this hypothetical protein and biochemical characterization enabled unambiguous assignment of this hypothetical protein as a NagZ. The identification and cloning of this NagZ may facilitate the development of strategies to circumvent resistance to beta-lactams in this human pathogen. As well, this general strategy, involving such 5-fluoro inactivators, may prove to be of general use for profiling proteomes and identifying glycoside hydrolases of medical importance or having desirable properties for biotechnology.

  DOI：

  10.1021/ja0763605