2,6-anhydro-1,3-O-p-anisylidene-5,7-O-benzylidene-4-O-(methylthio)methyl-D-glicero-L-manno-heptitol | 83654-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2,6-anhydro-1,3-O-p-anisylidene-5,7-O-benzylidene-4-O-(methylthio)methyl-D-glicero-L-manno-heptitol
• CAS: 83654-30-2
• 化学式: C₂₄H₂₈O₇S
• 分子量: 460.548
• InChiKey: VEEPUUFLWRHQMG-MKTXAMLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2,6-anhydro-1,3-O-p-anisylidene-5,7-O-benzylidene-D-glycero-L-manno-heptitol 、 二甲基亚砜 在 乙酸酐 作用下， 反应 48.0h， 以14%的产率得到2,6-anhydro-1,3-O-p-anisylidene-5,7-O-benzylidene-4-O-(methylthio)methyl-D-glicero-L-manno-heptitol
  参考文献：
  名称：

  Attempted affinity-labelling of β-d-galactosidase from Escherichia coli with 2,6:3,4-dianhydro-1-deoxy-d-talo-hept-1-enitol

  摘要：

  The epoxides methyl 2,3-anhydro-beta-D-talopyranoside (1) and 2,6:3,4-dianhydro-1-deoxy-D-talo-hept-1-enitol (2), both prepared by improved methods, and 2,6:3,4-dianhydro-1-deoxy-D-gulo-hept-1-enitol (3) were applied as potential reagents for the affinity labelling of E. coli beta-D-galactosidase. Compounds 1 and 3 are ineffective as labelling reagents, whereas compound 2 irreversibly inhibits the enzyme activity. Deactivation is complete only when high concentrations (0.5M) of the inhibitor are applied over a relatively long period of time (24 h). Saturation kinetics cannot be observed. Nevertheless, the competitive inhibitor isopropyl 1-thio-beta-D-galactopyranoside protects the enzyme from irreversible deactivation by 2, indicating that the latter also reacts with the active site. Treatment of beta-D-galactosidase with 2,6:3,4-dianhydro-1-deoxy-D-talo-[4-3H]hept-1-enitol under conditions that effect deactivation of the enzyme to only a minor extent causes labelling of the protein at the molar ratio of 48:1. Specific, radioaffinity labelling of the active site of the enzyme cannot be thus achieved.

  DOI：

  10.1016/s0008-6215(00)80774-0