1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosiduronic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosiduronic acid
• 英文别名: Pentan-3-Yl 2-(Acetylamino)-2,4-Dideoxy-Alpha-L-Threo-Hex-4-Enopyranosiduronic Acid；(2R,3R,4S)-3-acetamido-4-hydroxy-2-pentan-3-yloxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: UUULUCUBSUJBNQ-UFGOTCBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosiduronic acid 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以38%的产率得到1-(pent-3-yl) 2-acetamido-3-O-acetyl-2,4-dideoxy-α-L-threo-hex-4-enopyranosiduronic acid
  参考文献：
  名称：

  Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase

  摘要：

  A series of C3 O-functionalized 2-acetamido-2-deoxy-Delta(4)-beta-D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-mu M level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.

  DOI：

  10.1021/jm301145k
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium bromide 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 176.25h， 生成 1-(pent-3-yl) 2-acetamido-2,4-dideoxy-α-L-threo-hex-4-enopyranosiduronic acid
  参考文献：
  名称：

  Exploring the Interactions of Unsaturated Glucuronides with Influenza Virus Sialidase

  摘要：

  A series of C3 O-functionalized 2-acetamido-2-deoxy-Delta(4)-beta-D-glucuronides were synthesized to explore noncharge interactions in subsite 2 of the influenza virus sialidase active site. In complex with A/N8 sialidase, the parent compound (C3 OH) inverts its solution conformation to bind with all substituents well positioned in the active site. The parent compound inhibits influenza virus sialidase at a sub-mu M level; the introduction of small alkyl substituents or an acetyl group at C3 is also tolerated.

  DOI：

  10.1021/jm301145k

文献信息

• An efficient approach to N-acetyl-d-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors
  作者：Maretta C. Mann、Robin J. Thomson、Mark von Itzstein

  DOI：10.1016/j.bmcl.2004.08.064

  日期：2004.11

  the synthesis of beta-glycosides of N-acetyl-D-glucosaminuronic acid, in six steps and good overall yield from N-acetyl-d-glucosamine, has been developed. The key synthetic step was the Lewis acid mediated O-glycosidation of methyl 1,3,4-tri-O-pivaloyl-N-acetyl-D-glucosaminuronate (11). Elaboration of glucosaminuronides 15 and 18 provided novel sialylmimetics 21 and 22, which showed inhibition of Vibrio

  已经开发出一种新颖的方法，该方法以六个步骤合成了N-乙酰基-D-葡萄糖氨基糖醛酸的β-糖苷，并且从N-乙酰基-d-葡糖胺获得了良好的总收率。关键的合成步骤是路易斯酸介导的1,3,4-三-O-新戊酰基-N-乙酰基-D-氨基葡萄糖氨基磺酸甲酯的O-糖基化作用（11）。精心设计的葡糖氨基核苷15和18提供了新的唾液酸模拟物21和22，其显示了霍乱弧菌唾液酸酶的抑制作用。