5-N,6-S-[N'-(4-dansylamino)butyliminomethylidene]-6-thionojirimycin | 1257263-15-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-N,6-S-[N'-(4-dansylamino)butyliminomethylidene]-6-thionojirimycin
• 英文别名: 5-N,6-S-[N''-(4-Dansylamino)butyliminomethylidene]-6-thionojirimycin；N-[4-[[(5R,6R,7S,8R,8aS)-5,6,7,8-tetrahydroxy-1,5,6,7,8,8a-hexahydro-[1,3]thiazolo[3,4-a]pyridin-3-ylidene]amino]butyl]-5-(dimethylamino)naphthalene-1-sulfonamide
• CAS: 1257263-15-2
• 化学式: C₂₃H₃₂N₄O₆S₂
• 分子量: 524.662
• InChiKey: GSYZNUBEFOENOW-MIUGBVLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  180
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-N,6-S-[N'-(4-amino)butyliminomethylidene]-6-thio-nojirimycin hydrochloride 、 丹酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以98%的产率得到5-N,6-S-[N'-(4-dansylamino)butyliminomethylidene]-6-thionojirimycin
  参考文献：
  名称：

  Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity

  摘要：

  New fluorescently-labelled sp(2)-iminosugars based on the 5N,6S-[N'-(4-aminobutyl)iminomethylidene]-6-thionojirimycin skeleton have been synthesized as photoprobes to monitor glycosidase binding. Dansyl, dapoxyl and coumarin fluorophores were appended to the terminal amino group at the N'-substituent by either sulfonamide or amide bridging reaction. All the conjugates behaved as strong (low micromolar to nanomolar) and selective inhibitors of beta-glucosidases (almonds and bovine liver) and naringinase, in agreement with the inhibition pattern previously encountered for related iso(thio)urea-type bicyclic sp(2)-iminosugars. The presence of the fluorescent probe allows real-time and continuous monitoring of beta-glucosidase inhibition by fluorescence resonance energy transfer (FRET), taking advantage of the intrinsic tryptophan-associated fluorescence of the protein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.003

文献信息

• Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity
  作者：Matilde Aguilar-Moncayo、M. Isabel García-Moreno、Arnold E. Stütz、José M. García Fernández、Tanja M. Wrodnigg、Carmen Ortiz Mellet

  DOI：10.1016/j.bmc.2010.09.003

  日期：2010.11

  New fluorescently-labelled sp(2)-iminosugars based on the 5N,6S-[N'-(4-aminobutyl)iminomethylidene]-6-thionojirimycin skeleton have been synthesized as photoprobes to monitor glycosidase binding. Dansyl, dapoxyl and coumarin fluorophores were appended to the terminal amino group at the N'-substituent by either sulfonamide or amide bridging reaction. All the conjugates behaved as strong (low micromolar to nanomolar) and selective inhibitors of beta-glucosidases (almonds and bovine liver) and naringinase, in agreement with the inhibition pattern previously encountered for related iso(thio)urea-type bicyclic sp(2)-iminosugars. The presence of the fluorescent probe allows real-time and continuous monitoring of beta-glucosidase inhibition by fluorescence resonance energy transfer (FRET), taking advantage of the intrinsic tryptophan-associated fluorescence of the protein. (C) 2010 Elsevier Ltd. All rights reserved.