N-乙酰基葡萄糖胺-1-磷酸酯 | 6866-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-乙酰基葡萄糖胺-1-磷酸酯
• 英文名称: [13C]-N-acetylglucosamine-1-phosphate
• 英文别名: N-acetylglucosamine 1-phosphate；N-acetylglucosamine-1-phosphate；GlcNAc-1'-phosphate；N-acetyl-D-glucosamine-1-phosphate；[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
• CAS: 6866-69-9
• 化学式: C₈H₁₆NO₉P
• 分子量: 301.19
• InChiKey: FZLJPEPAYPUMMR-RTRLPJTCSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  166.6 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

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：

  尿苷-5'-三磷酸 、 N-乙酰基葡萄糖胺-1-磷酸酯 在 yeast inorganic pyrophosphatase 、 recombinant Arabidopsis N-acetylglucosamine-1-phosphate uridylyltransferase-1 、 magnesium chloride 作用下， 反应 0.07h， 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：

  在拟南芥属中严格和混杂的N-乙酰氨基葡萄糖-1-P uridylyltransferase的鉴定和表征。

  摘要：

  UDP-GlcNAc是糖蛋白和糖脂合成的重要前体。在本研究中，鉴定了来自拟南芥的编码58.3 kDa GlcNAc1pUT-1（N-乙酰氨基葡萄糖-1-磷酸尿嘧啶转移酶）的功能性核苷酸转移酶基因。在正向反应中，酶催化由相应的单糖1-磷酸酯和UTP形成UDP-N-乙酰氨基葡萄糖和PPi。该酶也可以利用4-表位UDP-GalNAc作为底物。该酶需要二价离子（Mg2 +或Mn2 +）才能发挥活性，并且在pH 6.5和8.0之间以及30-37摄氏度下具有很高的活性。正向反应的表观Km值为337 microM（GlcNAc-1-P）和295。 microM（UTP）。发现与GlcNAc1pUT-1具有86％氨基酸序列同一性的另一个GlcNAc1pUT-2可以转化，除了GlcNAc-1-P和GalNAc-1-P之外，Glc-1-P进入相应的UDP糖中，表明UT家族的细微变化会导致不同的底物特异性。尽管

  DOI：

  10.1042/bj20100315
• 作为产物：
  描述：

  D-glucosamine-1-phosphate 、 乙酰辅酶A 在 glucosamine-1-phosphate acetyltransferase 作用下， 生成 N-乙酰基葡萄糖胺-1-磷酸酯
  参考文献：
  名称：

  GlmU inhibitor from the roots of Euphorbia ebracteolata as an anti-tuberculosis agent

  摘要：

  经鉴定，白术素 F是从大戟科植物白术中提取的一种 GlmU 抑制剂，可抑制 M. tb H37Ra 的细胞壁生物合成和生物膜形成。

  DOI：

  10.1039/d2ra02044k

文献信息

• METHOD FOR PRODUCING N-ACETYL-D-GLUCOSAMINE AND/OR D-GLUCOSAMINE HYDROCHLORIDE BY MICROBIAL FERMENTATION
  申请人：Sun, Lan

  公开号：EP3441473A1

  公开（公告）日：2019-02-13

  This Invention discloses a method for production of N-Acetyl-D-Glucosamine and/or D-Glucosamine Salt by microbial fermentation. The method is intended to manufacture N-Acetyl-D-Glucosamine and/or D-Glucosamine Salt in higher efficiency and higher yield, by expression of vitreoscilla hemoglobin in microorganism.

  本发明公开了一种通过微生物发酵生产N-乙酰基-D-葡萄糖胺和/或D-葡萄糖胺盐的方法。该方法旨在通过在微生物中表达玻璃体血红蛋白，以更高的效率和产量生产 N-乙酰基-D-氨基葡萄糖和/或 D-氨基葡萄糖盐。
• Lipid-derived neutral nanoparticles
  申请人：TRANSLATE BIO, INC.

  公开号：US10137086B2

  公开（公告）日：2018-11-27

  Disclosed herein are novel lipids and liposomal compositions prepared using such compounds and related methods of neutralizing or otherwise modifying such liposomal compositions. The lipids described herein are useful for example, as liposomal vehicles to facilitate the delivery of encapsulated polynucleotides to target cells and the subsequent transfection of such target cells. In certain embodiments, one or more of the compounds that comprise the liposomal delivery vehicle may be neutralized or further modified such that the properties of the liposomal delivery vehicle are modified.

  本文公开了新型脂质和使用此类化合物制备的脂质体组合物，以及中和或以其他方式修饰此类脂质体组合物的相关方法。例如，本文所述的脂质可用作脂质体载体，以促进将封装的多核苷酸递送到靶细胞并随后转染这些靶细胞。在某些实施方案中，可对组成脂质体递送载体的一种或多种化合物进行中和或进一步修饰，从而改变脂质体递送载体的性质。
• Microbial fermentation method for production of n-acetyl-d-glucosamine and/or d-glucosamine salt
  申请人：Sun Lan

  公开号：US11136608B2

  公开（公告）日：2021-10-05

  This Invention discloses a method for production of N-Acetyl-D-Glucosamine and/or D-Glucosamine Salt by microbial fermentation. The method is intended to manufacture N-Acetyl-D-Glucosamine and/or D-Glucosamine Salt in higher efficiency and higher yield, by expression of vitreoscilla hemoglobin in microorganism.

  本发明公开了一种通过微生物发酵生产N-乙酰基-D-葡萄糖胺和/或D-葡萄糖胺盐的方法。该方法旨在通过在微生物中表达玻璃体血红蛋白，以更高的效率和产量生产 N-乙酰基-D-氨基葡萄糖和/或 D-氨基葡萄糖盐。
• Bacterial test method by glycated label binding
  申请人：Pugia J. Michael

  公开号：US20060141546A1

  公开（公告）日：2006-06-29

  A method for measuring the bacteria content of fluids such as urine and blood, in which a glycoprotein or glycopeptide is attached to the bacteria and a label attached to or inherent to the glycoprotein or glycopeptide provides a means for determining the amount of bacteria present. A preferred glycoprotein is alkaline phosphatase, which is an enzyme capable of attaching to all bacteria present in the fluid sample and inherently includes a label moiety in that color can be developed by addition of known reagents.

  一种测量尿液和血液等液体中细菌含量的方法，在这种方法中，糖蛋白或糖肽附着在细菌上，糖蛋白或糖肽上附着或固有的标签提供了一种确定细菌数量的方法。首选的糖蛋白是碱性磷酸酶，它是一种能够附着在液体样本中所有细菌上的酶，本身包括一个标签分子，通过添加已知试剂可以显色。
• In Vitro Validation of Acetyltransferase Activity of GlmU as an Antibacterial Target in Haemophilus influenzae
  作者：Ed T. Buurman、Beth Andrews、Ning Gao、Jun Hu、Thomas A. Keating、Sushmita Lahiri、Ludovic R. Otterbein、Arthur D. Patten、Suzanne S. Stokes、Adam B. Shapiro

  DOI：10.1074/jbc.m111.274068

  日期：2011.11

  GlmU is a bifunctional enzyme that is essential for bacterial growth, converting D-glucosamine 1-phosphate into UDP-GlicNAc via acetylation and subsequent uridyl transfer. A biochemical screen of AstraZeneca's compound library using GlmU of Escherichia coli identified novel sulfonamide inhibitors of the acetyltransferase reaction. Steady-state kinetics, ligand-observe NMR, isothermal titration calorimetry, and x-ray crystallography showed that the inhibitors were competitive with acetyl-CoA substrate. Iterative chemistry efforts improved biochemical potency against Gram-negative isozymes 300-fold and afforded antimicrobial activity against a strain of Haemophilus influenzae lacking its major efflux pump. Inhibition of precursor incorporation into bacterial macromolecules was consistent with the antimicrobial activity being caused by disruption of peptidoglycan and fatty acid biosyntheses. Isolation and characterization of two different resistant mutant strains identified the GlmU acetyltransferase domain as the molecular target. These data, along with x-ray co-crystal structures, confirmed the binding mode of the inhibitors and explained their relative lack of potency against Gram-positive GlmU isozymes. This is the first example of antimicrobial compounds mediating their growth inhibitory effects specifically via Glut U.