4-O-acetyl-2,6-anhydro-5,7-O-benzylidene-1,3-di-O-p-tolylsulfonyl-D-glycero-L-manno-heptitol | 83654-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-acetyl-2,6-anhydro-5,7-O-benzylidene-1,3-di-O-p-tolylsulfonyl-D-glycero-L-manno-heptitol
• CAS: 83654-29-9
• 化学式: C₃₀H₃₂O₁₁S₂
• 分子量: 632.709
• InChiKey: VCGRMYOWYLWHPJ-KWGIKKPDSA-N

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-2,6-anhydro-5,7-O-benzylidene-1,3-di-O-p-tolylsulfonyl-D-glycero-L-manno-heptitol 在 溶剂黄146 作用下， 反应 2.0h， 生成 Acetic acid (2R,3S,4S,5S,6S)-3-hydroxy-2-hydroxymethyl-5-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
  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
• 作为产物：
  描述：

  4-O-acetyl-2,6-anhydro-5,7-O-benzylidene-D-glycero-L-manno-heptitol 、 对甲苯磺酰氯 以 吡啶 为溶剂， 以84%的产率得到4-O-acetyl-2,6-anhydro-5,7-O-benzylidene-1,3-di-O-p-tolylsulfonyl-D-glycero-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