6-trifluoroacetamido-hexanol 1-phosphate triethylammonium salt

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 6-trifluoroacetamido-hexanol 1-phosphate triethylammonium salt
• 英文别名: N,N-diethylethanamine;6-[(2,2,2-trifluoroacetyl)amino]hexyl dihydrogen phosphate
• 化学式: C₆H₁₅N*C₈H₁₅F₃NO₅P
• 分子量: 394.372
• InChiKey: KPOIWOCZZFUNPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-trifluoroacetamido-hexanol 1-phosphate triethylammonium salt 在 ammonium hydroxide 、 N,N-二甲基苯胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 8.25h， 生成 GDP-hexanolamine
  参考文献：
  名称：

  An efficient synthesis of GDP-hexanolamine, a key tool for the purification of fucosyltransferases

  摘要：

  A new efficient synthesis of GDP-hexanolamine from hexanolamine is reported with an overall yield of 71%. The pyrophosphate formation, the key step of this preparation, was achieved through a sequential GMP activation procedure based on polytrifuoroacetylation of GMP followed by activation of the phosphate group by 1-methylimidazole. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(02)00105-2
• 作为产物：
  描述：

  三乙胺 、 1-O-(dibenzyl phosphoryloxy-6-trifluoroacetamido-1-hexanol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 6-trifluoroacetamido-hexanol 1-phosphate triethylammonium salt
  参考文献：
  名称：

  An efficient synthesis of GDP-hexanolamine, a key tool for the purification of fucosyltransferases

  摘要：

  A new efficient synthesis of GDP-hexanolamine from hexanolamine is reported with an overall yield of 71%. The pyrophosphate formation, the key step of this preparation, was achieved through a sequential GMP activation procedure based on polytrifuoroacetylation of GMP followed by activation of the phosphate group by 1-methylimidazole. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(02)00105-2

文献信息

• INHIBITORS OF UDP-GALACTOPYRANOSE MUTASE THWART MYCOBACTERIAL GROWTH
  申请人：Kiessling Laura Lee

  公开号：US20100056586A1

  公开（公告）日：2010-03-04

  Compounds which inhibit microbial growth or attenuate the virulence of pathogen microorganisms. Compounds of the invention inhibit UDP-galactopyranose mutase (UGM) and have activity as inhibitors of microbial growth of microorganisms which contain this enzyme and particularly those microorganisms in which this enzyme is responsible for the incorporation of galactofuranose residues, particularly for uridine 5′-diphosphate (UDP) galactopyranose mutase. Compounds of the invention inhibit UDP-galactopyranose mutase (UGM) and have activity to attenuate virulence of pathogenic microorganisms, including mycobacteria.

  本发明的化合物抑制微生物生长或减弱病原微生物的毒力。该发明的化合物抑制UDP半乳糖吡喃酮异构酶（UGM）并具有抑制含有该酶的微生物生长的活性，特别是对于该酶负责加入半乳糖呋喃糖残基的微生物，特别是对于尿苷5'-二磷酸（UDP）半乳糖吡喃酮异构酶。该发明的化合物抑制UDP半乳糖吡喃酮异构酶（UGM）并具有减弱病原微生物，包括分枝杆菌的毒力的活性。
• US8273778B2
  申请人：——

  公开号：US8273778B2

  公开（公告）日：2012-09-25
• Potent Ligands for Prokaryotic UDP-Galactopyranose Mutase That Exploit an Enzyme Subsite
  作者：Emily C. Dykhuizen、Laura L. Kiessling

  DOI：10.1021/ol802094p

  日期：2009.1.1

  UDP-Galactopyranose mutase (UGM or Glf), which catalyzes the interconversion of UDP-galactopyranose and UDP-galactofuranose, is implicated in the viability and virulence of multiple pathogenic microorganisms. Here we report the synthesis of high-affinity ligands for UGM homologues from Klebsiella pneumoniae and Mycobacterium tuberculosis. The potency of these compounds stems from their ability to access both the substrate binding pocket and an adjacent site.
• An efficient synthesis of GDP-hexanolamine, a key tool for the purification of fucosyltransferases
  作者：Stéphane P Vincent、Louis N Gastinel

  DOI：10.1016/s0008-6215(02)00105-2

  日期：2002.6

  A new efficient synthesis of GDP-hexanolamine from hexanolamine is reported with an overall yield of 71%. The pyrophosphate formation, the key step of this preparation, was achieved through a sequential GMP activation procedure based on polytrifuoroacetylation of GMP followed by activation of the phosphate group by 1-methylimidazole. (C) 2002 Published by Elsevier Science Ltd.