morphine 3-β-D-glucuronide NHS ester | 1314131-18-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: morphine 3-β-D-glucuronide NHS ester
• 英文别名: M3G-NHS-ester
• CAS: 1314131-18-4
• 化学式: C₂₇H₃₀N₂O₁₁
• 分子量: 558.542
• InChiKey: BQONHUDPUUJVPG-NPNJAHLQSA-N

反应信息

• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 吗啡-3-Β-D-葡糖苷酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 morphine 3-β-D-glucuronide NHS ester
  参考文献：
  名称：

  Characterization of Morphine–Glucose-6-phosphate Dehydrogenase Conjugates by Mass Spectrometry

  摘要：

  A key characteristic of the analyte-reporter enzyme conjugate used in the enzyme-multiplied immunoassay technique (EMIT) is the inhibition of the conjugate enzyme upon anti-analyte antibody binding. To improve our understanding of the antibody-induced inhibition mechanism, we characterized morphine-glucose-6-phosphate dehydrogenase (G6PDH) conjugates as model EMIT analyte-reporter enzyme conjugates. Morphine-G6PDH conjugates were prepared by acylating predominantly the primary amines on G6PDH with morphine 3-glucuronide NHS ester molecules. In this study, morphine-G6PDH conjugates were characterized using a combination of methods, including tryptic digestion, immunoprecipitation, matrix-assisted laser desorption ionization mass spectrometry, and electrospray ionization tandem mass spectrometry. Twenty-six conjugation sites were identified. The identified sites all were found to be primary amines. The degree of conjugation was determined to be less than the number of conjugation sites, suggesting heterogeneity within the morphine-G6PDH conjugate population. Two catalytically important residues in the active site (K22 and K183) were among the identified conjugation sites, explaining at least partially the cause of loss of activity due to the coupling reaction.

  DOI：

  10.1021/bc2001352