D-glucosamine-1-phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glucosamine-1-phosphate
• 英文别名: glucosamine-1-P；D-Glucosamin-1-phosphorsaeure；glucosamine 1-phosphate；[(3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
• 化学式: C₆H₁₄NO₈P
• 分子量: 259.153
• InChiKey: YMJBYRVFGYXULK-IVMDWMLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  D-glucosamine-1-phosphate 在 无机焦磷酸酶 、 glucosamine-1-phosphate acetyltransferase/N-acetylglucosamine-1-phosphate uridyltransferase 、 三乙胺 、 magnesium chloride 、 Cleland's reagent 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 UDP-GlcNTFA
  参考文献：
  名称：

  Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*

  摘要：

  Heparan sulfate is a sulfated glycan that exhibits essential physiological functions. Interrogation of the specificity of heparan sulfate-mediated activities demands a library of structurally defined oligosaccharides. Chemical synthesis of large heparan sulfate oligosaccharides remains challenging. We report the synthesis of oligosaccharides with different sulfation patterns and sizes from a disaccharide building block using glycosyl-transferases, heparan sulfate C-5-epimerase, and sulfotransferases. This method offers a generic approach to prepare heparan sulfate oligosaccharides possessing predictable structures.

  DOI：

  10.1074/jbc.m110.159152

文献信息

• [EN] LPXH TARGETING COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF MAKING AND USING THE SAME<br/>[FR] COMPOSÉS DE CIBLAGE LPXH, LEURS COMPOSITIONS ET PROCÉDÉS DE FABRICATION ET D'UTILISATION ASSOCIÉS
  申请人：UNIV DUKE

  公开号：WO2021072369A1

  公开（公告）日：2021-04-15

  LpxH targeting compounds, compositions thereof, as well as methods for for making and using the same are disclosed herein. The LpxH target compounds typically have a structure pursuant to Formula (I) and/or a salt thereof, wherein Rb is selected from a single bond, C4 to C10 unsubstituted aryl, C4 to C10 substituted aryl, unsubstituted or substituted four to ten member heterocycle ring, C1 to C10 unsubstituted alkyl, and C1 to C10 substituted alkyl; Rc comprises hydrogen, halogen, -OH, -CO2CH3, -COOH, -CN2CF3, -CF3,-C2OH, -CONHOH, -CCOH, C4 to C10 unsubstituted aryl, C4 to C10 substituted aryl, unsubstituted or substituted four to ten member heterocycle ring, C1 to C10 unsubstituted alkyl, or C1 to C10 substituted alkyl; and Rd and Re are independently hydrogen, -OH, -COH, -COH, -COC, -COOH, Rf, or are taken together as an unsubstituted or substituted four to eight member nitrogen containing heterocycle ring.

  LpxH靶向化合物，其组合物，以及制备和使用这些化合物的方法在此披露。LpxH靶向化合物通常具有符合式(I)的结构和/或其盐，其中Rb从单键，C4到C10未取代芳基，C4到C10取代芳基，未取代或取代的四到十元杂环环，C1到C10未取代烷基，和C1到C10取代烷基中选择；Rc包括氢，卤素，-OH，-CO2CH3，-COOH，-CN2CF3，-CF3，-C2OH，-CONHOH，-CCOH，C4到C10未取代芳基，C4到C10取代芳基，未取代或取代的四到十元杂环环，C1到C10未取代烷基，或C1到C10取代烷基；而Rd和Re独立地是氢，-OH，-COH，-COH，-COC，-COOH，Rf，或作为未取代或取代的四到八元含氮杂环环一起取代。
• GlmU inhibitor from the roots of <i>Euphorbia ebracteolata</i> as an anti-tuberculosis agent
  作者：Xiuyan Han、Changming Chen、Honglei Wang、Jian Kang、Qiulong Yan、Yufang Ma、Wenxin Wang、Shan Wu、Chao Wang、Xiaochi Ma

  DOI：10.1039/d2ra02044k

  日期：——

  Ebractenoid F was identified to be a GlmU inhibitor from Euphorbia ebracteolata, which could inhibit the cell wall biosynthesis of M. tb H37Ra, along with the biofilm formation.

  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。
• 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。
• 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。
• 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.