UDP-GlcNAcA | 24758-79-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: UDP-GlcNAcA
• 英文别名: UDP-N-Ace；UDP-N-acetylglucosamine；UDP-N-acetyl-D-glucosaminuronic acid；UDP-GlcNAc；(2s,3s,4r,5r,6r)-5-Acetamido-6-[[[(2r,3s,4r,5r)-5-(2,4-Dioxopyrimidin-1-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-3,4-Dihydroxy-Oxane-2-Carboxylic Acid；(2S,3S,4R,5R,6R)-5-acetamido-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• CAS: 24758-79-0
• 化学式: C₁₇H₂₅N₃O₁₈P₂
• 分子量: 621.342
• InChiKey: DZOGQXKQLXAPND-HHKCBAECSA-N

物化性质

• 密度：
  1.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  318
• 氢给体数：
  9
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  UDP-GlcNAcA 在 DL-谷氨酸 、 5,5'-二硫双(2-硝基苯甲酸) 、 Bordetella petrii WlbB N-acetyltransferase 、 Bordetella petrii WlbC 、 Thermus thermophilus WlbA 作用下， 反应 12.0h， 生成 UDP-GlcNAc3NAcA
  参考文献：
  名称：

  Molecular Structure of WlbB, a Bacterial N-Acetyltransferase Involved in the Biosynthesis of 2,3-Diacetamido-2,3-dideoxy-d-mannuronic Acid,

  摘要：

  The pathogenic bacteria Pseudomonas aeruginosa and Bordetella pertussis contain in their outer membranes the rare sugar 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid. Five enzymes are required for the biosynthesis of this sugar starting from UDP-N-acetylglucosamine. One of these, referred to as WlbB, is an N-acetyltransferase that converts UDP-2-acetamido-3-amino-2,3-dideoxy-D-glucuronic acid (UDP-GlcNAc3NA) to UDP-2,3-diacetamido-2,3-dideoxy-D-glucuronic acid (UDP-GlcNAc3NAcA). Here we report the three-dimensional structure of WlbB from Bordetella petrii. For this analysis, two ternary structures were determined to 1.43 angstrom resolution: one in which the protein was complexed with acetyl-CoA and UDP and the second in which the protein contained bound CoA and UDP-GlcNAc3NA. WlbB adopts a trimeric quaternary structure and belongs to the L beta H superfamily of N-acyltransferases. Each subunit contains 27 beta-strands, 23 of which form the canonical left-handed beta-helix. There are only two hydrogen bonds that occur between the protein and the GlcNAc3NA moiety, one between O-delta 1 of Asn 84 and the sugar C-3' amino group and the second between the backbone amide group of Arg 94 and the sugar C-5' carboxylate. The sugar C-3' amino group is ideally positioned in the active site to attack the si face of acetyl-CoA. Given that there are no protein side chains that can function as general bases within the GlcNAc3NA binding pocket, a reaction mechanism is proposed for WlbB whereby the sulfur of CoA ultimately functions as the proton acceptor required for catalysis.

  DOI：

  10.1021/bi1005738
• 作为产物：
  描述：

  尿苷5'-(2-乙酰氨基-2-脱氧-ALPHA-D-葡糖基焦磷酸酯) 在 铂 氧气 作用下， 生成 UDP-GlcNAcA
  参考文献：
  名称：

  A fluorescent analogue of UDP-N-acetylglucosamine: application for FRET assay of peptidoglycan translocase II (MurG)

  摘要：

  利用 UDP-N-acetylglucosamine 的 6 取代荧光类似物，开发了一种基于荧光共振能量转移（FRET）的转运酶 II MurG 直接连续荧光测定法。

  DOI：

  10.1039/b313316h

文献信息

• A fluorescent analogue of UDP-N-acetylglucosamine: application for FRET assay of peptidoglycan translocase II (MurG)
  作者：Jian-Jun Li、Timothy D. H. Bugg

  DOI：10.1039/b313316h

  日期：——

  A direct continuous fluorescence assay for translocase II MurG based on fluorescence resonance energy transfer (FRET) has been developed using a 6-substituted fluorescent analogue of UDP-N-acetylglucosamine.

  利用 UDP-N-acetylglucosamine 的 6 取代荧光类似物，开发了一种基于荧光共振能量转移（FRET）的转运酶 II MurG 直接连续荧光测定法。
• Structural and Functional Studies of WlbA: A Dehydrogenase Involved in the Biosynthesis of 2,3-Diacetamido-2,3-dideoxy-<scp>d</scp>-mannuronic Acid,
  作者：James B. Thoden、Hazel M. Holden

  DOI：10.1021/bi101103s

  日期：2010.9.14

  3-Diacetamido-2,3-dideoxy-d-mannuronic acid (ManNAc3NAcA) is an unusual dideoxy sugar first identified nearly 30 years ago in the lipopolysaccharide of Pseudomonas aeruginosa O:3a,d. It has since been observed in other organisms, including Bordetella pertussis, the causative agent of whooping cough. Five enzymes are required for the biosynthesis of UDP-ManNAc3NAcA starting from UDP-N-acetyl-d-glucosamine. Here

  2,3-Diacetamido-2,3-dideoxy- d - mannuronic acid (ManNAc3NAcA) 是一种不寻常的双脱氧糖，近 30 年前首次在铜绿假单胞菌O:3a,d的脂多糖中被发现。此后在其他生物体中观察到它，包括百日咳的病原体百日咳博德特氏菌。五种酶所需的UDP-ManNAc3NAcA从UDP-起始生物合成Ñ乙酰基d -葡糖胺。在这里，我们描述了 WlbA 的结构研究，NAD 依赖性脱氢酶催化该途径的第二步，即将 UDP 连接的糖上的 C-3' 羟基氧化为酮基部分和 NAD 的还原+到 NADH。这种酶已被证明使用 α-酮戊二酸作为氧化剂来再生氧化的二核苷酸。在这项研究中，确定了三种不同的晶体结构：结合 NAD(H) 的酶、与 NAD(H) 和 α-酮戊二酸形成复合物的酶，以及与 NAD(H) 及其底物形成复合物的酶（ UDP- ñ乙酰基d -glucosa
• Cofactor‐Driven Cascade Reactions Enable the Efficient Preparation of Sugar Nucleotides
  作者：Yuan Zheng、Jiabin Zhang、Jeffrey Meisner、Wanjin Li、Yawen Luo、Fangyu Wei、Liuqing Wen

  DOI：10.1002/anie.202115696

  日期：2022.5.9

  The complex de novo biosynthesis of sugar nucleotides was reorganized as cascade reactions. The cascade reactions were driven toward the formation of the target sugar nucleotides through the addition of an excess amount of a cofactor provided by a cofactor regeneration system, thus resulting in high synthetic yields.

  糖核苷酸的复杂从头生物合成被重组为级联反应。通过添加辅因子再生系统提供的过量辅因子，将级联反应驱动到目标糖核苷酸的形成，从而产生高合成产量。
• Directing the biological activities of heparan sulfate oligosaccharides using a chemoenzymatic approach
  作者：Yongmei Xu、Zhen Wang、Renpeng Liu、Arlene S Bridges、Xuefei Huang、Jian Liu

  DOI：10.1093/glycob/cwr109

  日期：2012.1

  Heparan sulfate (HS) and heparin are highly sulfated polysaccharides exhibiting essential physiological functions. The sulfation patterns determine the functional selectivity for HS and heparin. Chemical synthesis of HS, especially those larger than a hexasaccharide, remains challenging. Enzymatic synthesis of HS has recently gained momentum. Here we describe the divergent assembly of HS heptasaccharides

  硫酸乙酰肝素 (HS) 和肝素是高度硫酸化的多糖，具有重要的生理功能。硫酸化模式决定了对 H2S 和肝素的功能选择性。HS 的化学合成，尤其是比六糖大的那些，仍然具有挑战性。HS 的酶促合成最近获得了动力。在这里，我们描述了来自常见六糖前体的 HS 七糖和九糖的不同组装。六糖前体是通过化学方法合成的。随后的延伸、硫酸化和差向异构化由糖基转移酶、HS磺基转移酶和差向异构酶完成。使用合成的七糖，我们发现艾杜糖醛酸对于与成纤维细胞生长因子 2 的结合至关重要。我们还设计了一种合成途径来制备抗凝血酶结合亲和力为 3 nM 的九糖。我们的方法证明了将化学合成和酶促合成相结合以制备具有所需生物活性的结构定义的 HS 寡糖的可行性。
• Molecular Structure of WlbB, a Bacterial <i>N</i>-Acetyltransferase Involved in the Biosynthesis of 2,3-Diacetamido-2,3-dideoxy-<scp>d</scp>-mannuronic Acid,
  作者：James B. Thoden、Hazel M. Holden

  DOI：10.1021/bi1005738

  日期：2010.6.8

  The pathogenic bacteria Pseudomonas aeruginosa and Bordetella pertussis contain in their outer membranes the rare sugar 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid. Five enzymes are required for the biosynthesis of this sugar starting from UDP-N-acetylglucosamine. One of these, referred to as WlbB, is an N-acetyltransferase that converts UDP-2-acetamido-3-amino-2,3-dideoxy-D-glucuronic acid (UDP-GlcNAc3NA) to UDP-2,3-diacetamido-2,3-dideoxy-D-glucuronic acid (UDP-GlcNAc3NAcA). Here we report the three-dimensional structure of WlbB from Bordetella petrii. For this analysis, two ternary structures were determined to 1.43 angstrom resolution: one in which the protein was complexed with acetyl-CoA and UDP and the second in which the protein contained bound CoA and UDP-GlcNAc3NA. WlbB adopts a trimeric quaternary structure and belongs to the L beta H superfamily of N-acyltransferases. Each subunit contains 27 beta-strands, 23 of which form the canonical left-handed beta-helix. There are only two hydrogen bonds that occur between the protein and the GlcNAc3NA moiety, one between O-delta 1 of Asn 84 and the sugar C-3' amino group and the second between the backbone amide group of Arg 94 and the sugar C-5' carboxylate. The sugar C-3' amino group is ideally positioned in the active site to attack the si face of acetyl-CoA. Given that there are no protein side chains that can function as general bases within the GlcNAc3NA binding pocket, a reaction mechanism is proposed for WlbB whereby the sulfur of CoA ultimately functions as the proton acceptor required for catalysis.