Methyl 5-acetamido-4,7,8-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-9-O-(4-tolylsulfonyl)-D-glycero-D-galacto-non-2-enonate | 112824-45-0

• 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: Methyl 5-acetamido-4,7,8-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-9-O-(4-tolylsulfonyl)-D-glycero-D-galacto-non-2-enonate
• CAS: 112824-45-0
• 化学式: C₂₅H₃₁NO₁₃S
• 分子量: 585.586
• InChiKey: BBQFOKNHTHSMLH-ISQZKQDNSA-N

反应信息

• 作为反应物：
  描述：

  Methyl 5-acetamido-4,7,8-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-9-O-(4-tolylsulfonyl)-D-glycero-D-galacto-non-2-enonate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以51%的产率得到(4S,5R,6S)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,2-diacetoxy-3-azido-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Distinguishing mammalian sialidases by inhibition kinetics with novel derivatives of 5-acetamido-2,6-anhydro-3,5-dideoxy-d-glycero-d-galacto-non-2-enonic acid, an unsaturated derivative of N-acetylneuraminic acid

  摘要：

  Kinetic analysis of mammalian sialidases was carried out using analogs of the potent sialidase inhibitor, 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonic acid (1). Substituents at C-9 in place of the terminal hydroxyl group included a, 4-azido-2-nitrophenylthio group to give 5-acetamido-2,6-anhydro-9-S-(4-azido-2-nitrophenyl)-3,5,9-trideoxy-9-thio-D-glycero-D-galacto-non-2-enonic acid (2), and an azide group to give 5-acetamido-2,6-anhydro-9-azido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid (3). Competitive inhibition kinetics were observed when 1,2, and 3 were tested with the lysosomal sialidase (cultured fibroblasts) and the plasma membrane sialidase (adenovirus DNA-transformed, human embryonic kidney cells), giving a K(i) of about 10-mu-M for both enzymes with all three compounds. In contrast, only 1 was a potent inhibitor of the microsomal sialidase (rat muscle).

  DOI：

  10.1016/0008-6215(91)84030-i