cyclohexyl 2-deoxy-2-methanesulfonamido-1-thio-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexyl 2-deoxy-2-methanesulfonamido-1-thio-α-D-glucopyranoside
• 英文别名: N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)methanesulfonamide；N-[(2R,3R,4R,5S,6R)-2-cyclohexylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]methanesulfonamide
• 化学式: C₁₃H₂₅NO₆S₂
• 分子量: 355.477
• InChiKey: APPRGZFSBHQCMQ-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-(cyclohexylthio)-5-(methylsulfonamido)-tetrahydro-2H-pyran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 cyclohexyl 2-deoxy-2-methanesulfonamido-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Natural Product-Inspired Inhibitors of Mycobacterium tuberculosis Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase

  摘要：

  Synthesis and evaluation of a chemical library of inhibitors of the mycothiol biosynthesis enzyme GlcNAc-Ins deacetylase (MshB) and the mycothiol-dependent detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis are reported. The library was biased to include structural features of a group of natural products previously shown to competitively inhibit MCA. Molecular docking studies that reproducibly placed the inhibitors in the active site of the enzyme MshB reveal the mode of binding and are consistent with observed biological activity.

  DOI：

  10.1021/jm070669h

文献信息

• A Family of Mycothiol Analogues
  作者：Spencer Knapp、Benjamin Amorelli、Etzer Darout、Christian C. Ventocilla、Lawrence M. Goldman、Richard A. Huhn、Ellen C. Minnihan

  DOI：10.1081/car-200059965

  日期：2005.3

  A thioglycoside aminotriol scaffold has been elaborated by acylation, reductive alkylation, sulfonation, phosphorylation, and other procedures to produce a library of 40 functionalized thioglycosides that superficially resemble the enzyme-binding portions of the Mycobacterium tuberculosis detoxifier mycothiol and its metabolic congeners. To the extent that these analogues mimic the transition states derived from substrates of the mycothiol-associated enzymes, they might prove useful as inhibitors and, ultimately, as drug leads.
• Synthesis of Natural Product-Inspired Inhibitors of <i>Mycobacterium tuberculosis</i> Mycothiol-Associated Enzymes: The First Inhibitors of GlcNAc-Ins Deacetylase
  作者：Belhu B. Metaferia、Brandon J. Fetterolf、Syed Shazad-ul-Hussan、Matthew Moravec、Jeremy A. Smith、Satyajit Ray、Maria-Teresa Gutierrez-Lugo、Carole A. Bewley

  DOI：10.1021/jm070669h

  日期：2007.12.13

  Synthesis and evaluation of a chemical library of inhibitors of the mycothiol biosynthesis enzyme GlcNAc-Ins deacetylase (MshB) and the mycothiol-dependent detoxification enzyme mycothiol-S-conjugate amidase (MCA) from Mycobacterium tuberculosis are reported. The library was biased to include structural features of a group of natural products previously shown to competitively inhibit MCA. Molecular docking studies that reproducibly placed the inhibitors in the active site of the enzyme MshB reveal the mode of binding and are consistent with observed biological activity.