N-acetylglucosamine-1-phosphate | 28446-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetylglucosamine-1-phosphate
• 英文别名: 2-acetamido-2-deoxy-α-D-glucose 1-phosphate；1-(α-D-N-acetylglucosamine) phosphate；(N-acetyl-α-D-glucosamine (1-P))；α-GlcNAc-(1->O)PO3H2；2-N-acetylglucosamine 1-phosphate；GlcNAc-1-phosphate；N-acetyl-alpha-D-glucosamine 1-phosphate；[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
• CAS: 28446-21-1
• 化学式: C₈H₁₆NO₉P
• 分子量: 301.19
• InChiKey: FZLJPEPAYPUMMR-FMDGEEDCSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-acetylglucosamine-1-phosphate 、 尿苷-5'-三磷酸 在 Pyrococcus furious enzyme 、 magnesium 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 尿苷5'-(2-乙酰氨基-2-脱氧-ALPHA-D-葡糖基焦磷酸酯)
  参考文献：
  名称：

  One-Step Synthesis of Labeled Sugar Nucleotides for Protein O-GlcNAc Modification Studies by Chemical Function Analysis of an Archaeal Protein

  摘要：

  Herein we present the chemical function analysis of a recombinant sugar nucleotidyltransferase from the hyperthermophile Pyrococcus furiosus and its use in the one-pot synthesis of chloroacetyl- and alkyne-tagged analogues of uridinediphospho-N-acetylglucosamine (UDP-GlcNAc). The gene was originally annotated as a glucose-1-phosphate deoxythymidylyltransferase; however, kinetic analysis of a panel of sugar-1-phosphates with the protein shows that it is better described as a bifunctional protein that synthesizes UDP-GlcNAc from glucosamine-1-phosphate and acetyl coenzyme A (CoA). A new mass-spectrometry-based assay for the rapid analysis of the acyltransferase activity demonstrates that the enzyme can also accept cheaper truncated N-acetylcysteamine thioester substrates in place of the natural acetyl CoA. The enzyme can tolerate alkyne or chloride substitutions in the acyl moiety, thereby allowing the facile synthesis of tagged sugar nucleotides for future use in protein O-GlcNAc modification studies.

  DOI：

  10.1021/ja044117p
• 作为产物：
  描述：

  D-GlcNAc 在 N-acetylglucosamine kinase (GlcK, C_. albicans) 、 N-acetylglucosamine phosphate mutase (Agm₁, S_. cerevisiae) 作用下， 生成 N-acetylglucosamine-1-phosphate
  参考文献：
  名称：

  多种酶共固定在琼脂糖珠上生物催化合成尿苷 5'-二磷酸 N-乙酰氨基葡萄糖

  摘要：

  重组 N-乙酰氨基葡萄糖激酶、丙酮酸激酶、N-乙酰氨基葡萄糖磷酸变位酶、尿苷 5'-二磷酸 N-乙酰氨基葡萄糖焦磷酸化酶和无机焦磷酸酶在大肠杆菌中过表达，并共同固定在琼脂糖珠上，用于实际合成尿苷 5'-二磷酸N-乙酰氨基葡萄糖。

  DOI：

  10.1039/b207480j

文献信息

• Active-site engineering of nucleotidylyltransferases and general enzymatic methods for the synthesis of natural and "unnatural" UDP- and TDP-nucleotide sugars
  申请人：——

  公开号：US20030055235A1

  公开（公告）日：2003-03-20

  The present invention provides mutant nucleotidylyl-transferases, such as E p , having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified Ep or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

  本发明提供了一种突变型核苷酸转移酶，如E p ，具有改变的底物特异性；其生产方法；以及利用这些核苷酸转移酶生产核苷酸糖的方法。本发明还提供了使用天然和/或修饰的Ep或其他核苷酸转移酶合成所需的核苷酸糖的方法；以及通过本发明方法合成的核苷酸糖。本发明进一步提供了新的糖基磷酸酯，及其制造方法。
• [EN] ACTIVATED N-ACETYLATED SUGARS AND OLIGOSACCHARIDES<br/>[FR] SUCRES ET OLIGOSACCHARIDES N-ACÉTYLÉS ACTIVÉS
  申请人：ZUCHEM INC

  公开号：WO2016205332A1

  公开（公告）日：2016-12-22

  The invention relates to production of uridine-5'diphospho-N-acetylglucosamine and uridine-5'diphospho-N-acetylgalactosamine. The invention further relates to the production of lacto-/V-triose II and globotetraose.

  该发明涉及尿苷-5'-二磷酸-N-乙酰葡萄糖胺和尿苷-5'-二磷酸-N-乙酰半乳糖胺的生产。该发明还涉及乳酸/ V-三糖II和球四糖的生产。
• NOVEL TLR4 INHIBITORS FOR THE TREATMENT OF HUMAN INFECTIOUS AND INFLAMMATORY DISORDERS
  申请人：System of Higher Education University of Pittsburgh - of the Commonwealth

  公开号：US20130281395A1

  公开（公告）日：2013-10-24

  The present invention relates to methods of treating infectious, inflammatory and post-traumatic disorders by administering various compounds newly discovered to have TLR4 inhibitory activity. In addition to methods of treatment, the present invention further provides for pharmaceutical compositions comprising said compounds, together with a suitable pharmaceutical carrier. Because TLR4 is the most upstream receptor in the pro-inflammatory LPS signaling cascade, treatments of the invention, which inhibit or antagonize TLR4 action, may avoid the pitfalls associated with other cytokine inhibitors that act further down the pathway and accordingly play a less specific (and perhaps non-critical) role.

  本发明涉及通过给予新发现具有TLR4抑制活性的各种化合物来治疗感染性、炎症性和创伤后疾病的方法。除了治疗方法外，本发明还提供了包括所述化合物在内的药物组合物，以及适当的药物载体。由于TLR4是促炎性LPS信号级联中最上游的受体，本发明的治疗方法可以通过抑制或拮抗TLR4的作用来避免与其他细胞因子抑制剂相关的缺陷，这些细胞因子抑制剂作用于信号通路中较下游的位置，因此起到了不太特异（也许是非关键）的作用。
• 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。
• ACTIVE-SITE ENGINEERING OF NUCLEOTIDYLYLTRANSFERASES AND GENERAL ENZYMATIC METHODS FOR THE SYNTHESIS OF NATURAL AND "UNNATURAL" UDP- AND TDP-NUCLEOTIDE SUGARS
  申请人：THORSON Jon

  公开号：US20070178487A1

  公开（公告）日：2007-08-02

  The present invention provides mutant nucleotidylyl-transferases, such as E p , having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified E p or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

  本发明提供了突变核苷酸转移酶，例如Ep，具有改变的底物特异性；其生产方法；以及利用这些核苷酸转移酶生产核苷酸糖的方法。本发明还提供了使用天然和/或改性的Epor或其他核苷酸转移酶合成所需核苷酸糖的方法；以及通过本方法合成的核苷酸糖。本发明还提供了新的糖基磷酸酯，以及制备它们的方法。