2-acetamido-2-deoxy-α-D-glucopyranosyl phosphate mono-cyclohexylammonium salt | 1013631-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-α-D-glucopyranosyl phosphate mono-cyclohexylammonium salt
• CAS: 1013631-00-9
• 化学式: C₆H₁₃N*C₈H₁₆NO₉P
• 分子量: 400.366
• InChiKey: UXXNQTDLGBNUIJ-TVLNMICESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.68
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  191.8
• 氢给体数：
  7.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-α-D-glucopyranosyl phosphate mono-cyclohexylammonium salt 、 uridine 5'-monophosphate morpholidate 在 MS 4 Angstroem 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以38%的产率得到2-acetamido-2-deoxy-α-D-glucosyl uridine diphosphate diammonium salt
  参考文献：
  名称：

  Gram-scale synthesis of uridine 5'-diphospho-N-acetylglucosamine: comparison of enzymic and chemical routes

  摘要：

  Practical chemoenzymatic and chemical routes to uridine 5'-diphospho-N-acetylglucosamine (UDP-GlcNAc) on a gram scale have been developed. The chemoenzymatic synthesis provided convenient access to glucosamine-6-phosphate and N-acetylglucosamine-6-phosphate (GlcNAc-6-P) in > 10-mmol quantities. The condensation between GlcNAc-6-P and UTP was catalyzed by readily available crude enzyme extracts from dried cells of the yeast Candida utilis and afforded a 17% yield of UDP-GlcNAc from GlcNAc-6-P. The otherwise straightforward chemoenzymatic sequence was hampered by the need to purify the product from the final complex reaction mixture. The chemical synthesis of UDP-GlcNAc proceeded through five steps in an overall yield of 15% from penta-acetylglucosamine with the selective formation of tetraacetylglucosamine-alpha-1-phosphate as the key reaction.

  DOI：

  10.1021/jo00027a028
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucosyl dicyclohexylammonium phosphate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以2.62 g的产率得到2-acetamido-2-deoxy-α-D-glucopyranosyl phosphate mono-cyclohexylammonium salt
  参考文献：
  名称：

  Gram-scale synthesis of uridine 5'-diphospho-N-acetylglucosamine: comparison of enzymic and chemical routes

  摘要：

  Practical chemoenzymatic and chemical routes to uridine 5'-diphospho-N-acetylglucosamine (UDP-GlcNAc) on a gram scale have been developed. The chemoenzymatic synthesis provided convenient access to glucosamine-6-phosphate and N-acetylglucosamine-6-phosphate (GlcNAc-6-P) in > 10-mmol quantities. The condensation between GlcNAc-6-P and UTP was catalyzed by readily available crude enzyme extracts from dried cells of the yeast Candida utilis and afforded a 17% yield of UDP-GlcNAc from GlcNAc-6-P. The otherwise straightforward chemoenzymatic sequence was hampered by the need to purify the product from the final complex reaction mixture. The chemical synthesis of UDP-GlcNAc proceeded through five steps in an overall yield of 15% from penta-acetylglucosamine with the selective formation of tetraacetylglucosamine-alpha-1-phosphate as the key reaction.

  DOI：

  10.1021/jo00027a028

文献信息

• Exploring specificity of glycosyltransferases: synthesis of new sugar nucleotide related molecules as putative donor substrates
  作者：Amira Khaled、Olga Piotrowska、Katarzyna Dominiak、Claudine Augé

  DOI：10.1016/j.carres.2007.11.009

  日期：2008.2

  with an IC50 value of 7 mM. In the second approach, we prepared sugar nucleotide mimics having the diphosphate bridge replaced by the oxycarbonylaminosulfonyl linker. The surrogate of GDP-Fuc was synthesized as a 9:1 alpha/beta anomeric mixture, in 40% yield, starting from chlorosulfonyl isocyanate, perbenzylated l-fucopyranose, and a guanosine derivative, protected on the exocyclic amine and secondary

  我们研究了糖基转移酶在两个互补方向上对供体底物的特异性。首先，我们准备了简单的N-乙酰基-α-D-氨基葡萄糖1-二磷酸酯：甲基-（2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基）-二磷酸酯，苄基-（2-乙酰氨基-2-脱氧-α-磷酸酯D-吡喃葡萄糖基）-二磷酸酯，4-苯基丁基-（2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基）-二磷酸酯，通过将相应的活化烷基磷酸酯与N-乙酰基-α-D-葡糖胺1-偶联磷酸盐。在脑膜炎奈瑟氏菌N-乙酰氨基葡萄糖氨基转移酶（LgtA）催化的反应中，作为N-乙酰氨基葡萄糖的供体，测试了这些二磷酸以及2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖1-二磷酸的活性。评估为抑制剂，只有2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖1-二磷酸酯显示出一定的抑制活性，IC50值为7 mM。在第二种方法中，我们准备了糖核苷酸模拟物，其二磷酸桥被氧羰基氨基磺酰基接头取代。GDP-Fuc的替代
• Facile enzymatic synthesis of sugar 1-phosphates as substrates for phosphorylases using anomeric kinases
  作者：Yuan Liu、Mamoru Nishimoto、Motomitsu Kitaoka

  DOI：10.1016/j.carres.2014.10.014

  日期：2015.1

  Three sugar 1-phosphates that are donor substrates for phosphorylases were produced at the gram scale from phosphoenolpyruvic acid and the corresponding sugars by the combined action of pyruvate kinase and the corresponding anomeric kinases in good yields. These sugar 1-phosphates were purified through two electrodialysis steps. α-D-Galactose 1-phosphate was finally isolated as crystals of dipotassium

  通过丙酮酸丙酮酸激酶和相应的端基异构激酶的联合作用，以良好的产率由磷酸烯醇丙酮酸和相应的糖以克规模产生了三种磷酸1-磷酸酯，它们是磷酸化酶的供体底物。这些糖1-磷酸酯通过两个电渗析步骤纯化。最终分离出作为双钾盐晶体的α-D-半乳糖1-磷酸酯。分离出作为双（环己基铵）盐晶体的α-D-甘露糖1-磷酸酯和2-乙酰氨基-2-脱氧-α-D-葡萄糖1-磷酸酯。