UDP-GlcNAc3NA | 868075-76-7

• 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-GlcNAc3NA
• 英文别名: UDP-2-acetamido-3-amino-2,3-dideoxy-alpha-D-glucuronic acid；(2S,3S,4R,5R,6R)-5-acetamido-4-amino-6-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3-hydroxyoxane-2-carboxylic acid
• CAS: 868075-76-7
• 化学式: C₁₇H₂₆N₄O₁₇P₂
• 分子量: 620.358
• InChiKey: RRAQYLXLCYIZBB-HHKCBAECSA-N

物化性质

• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -8.9
• 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：
  323
• 氢给体数：
  9
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  UDP-GlcNAc3NA 在 5,5'-二硫双(2-硝基苯甲酸) 、 Bordetella petrii WlbB N-acetyltransferase 、 WlbD 作用下， 生成 UDP-ManNAc3NAcA
  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：

  UDP-GlcNAcA 在 磷酸吡哆醛 、 monosodium glutamate 、 recombinant Psychrobacter cryohalolentis K₅^T nicotinamide adenine dinucleotide (oxidized) (NAD+)-dependent dehydrogenase 、 recombinant Psychrobacter cryohalolentis K₅^T pyridoxal 5'-phosphate (PLP)-dependent aminotransferase 作用下， 以 aq. buffer 为溶剂， 生成 UDP-GlcNAc3NA
  参考文献：
  名称：

  冷卤冷杆菌 K5T 生物合成 2,3-二乙酰氨基-2,3-二脱氧-d-葡萄糖醛酸所需酶的研究

  摘要：

  冷卤冷杆菌K5 T是一种革兰氏阴性细菌，于 2006 年首次从西伯利亚永久冻土中分离出来。它具有复杂的 O 抗原，含有L-鼠李糖、 D-半乳糖、两种二乙酰胺糖和一种三乙酰胺糖。其中一种二乙酰胺基糖，即2,3-二乙酰胺基-2,3-二脱氧-d-葡萄糖醛酸的生物合成途径目前尚不清楚。利用已发表的P.cryohalolentis K5 T基因组序列，我们假设Pcryo_0613 、 Pcryo_0614 、 Pcryo_0616和Pcryo_0615基因编码尿苷二核苷酸 (UDP) -N-乙酰基-d-葡萄糖胺 6-脱氢酶（一种烟酰胺腺嘌呤二核苷酸）分别是（氧化）（NAD + ）依赖性脱氢酶、5'-磷酸吡哆醛（PLP）依赖性氨基转移酶和N-乙酰转移酶，这些酶的活性是这种不寻常碳水化合物的生物合成所必需的。在这里，我们展示了这些假设蛋白质的克隆、过表达和纯化。 Pcryo_0613 、 Pcryo_0

  DOI：

  10.1002/pro.4502

文献信息

• 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.
• Investigation of the enzymes required for the biosynthesis of 2, <scp>3‐</scp> diacetamido‐2,3‐dideoxy‐ <scp>d</scp> ‐glucuronic acid in <i>Psychrobacter cryohalolentis</i> <scp> K5 ^T </scp>
  作者：Daniel L. Hofmeister、Chase A. Seltzner、Nicholas J. Bockhaus、James B. Thoden、Hazel M. Holden

  DOI：10.1002/pro.4502

  日期：2023.1

  cryohalolentis K5T, we hypothesized that the genes designated Pcryo_0613, Pcryo_0614, Pcryo_0616, and Pcryo_0615 encode for a uridine dinucleotide (UDP)-N-acetyl-d-glucosamine 6-dehydrogenase, an nicotinamide adenine dinucleotide (oxidized) (NAD+)-dependent dehydrogenase, a pyridoxal 5′-phosphate (PLP)-dependent aminotransferase, and an N-acetyltransferase, respectively, activities of which would be required

  冷卤冷杆菌K5 T是一种革兰氏阴性细菌，于 2006 年首次从西伯利亚永久冻土中分离出来。它具有复杂的 O 抗原，含有L-鼠李糖、 D-半乳糖、两种二乙酰胺糖和一种三乙酰胺糖。其中一种二乙酰胺基糖，即2,3-二乙酰胺基-2,3-二脱氧-d-葡萄糖醛酸的生物合成途径目前尚不清楚。利用已发表的P.cryohalolentis K5 T基因组序列，我们假设Pcryo_0613 、 Pcryo_0614 、 Pcryo_0616和Pcryo_0615基因编码尿苷二核苷酸 (UDP) -N-乙酰基-d-葡萄糖胺 6-脱氢酶（一种烟酰胺腺嘌呤二核苷酸）分别是（氧化）（NAD + ）依赖性脱氢酶、5'-磷酸吡哆醛（PLP）依赖性氨基转移酶和N-乙酰转移酶，这些酶的活性是这种不寻常碳水化合物的生物合成所必需的。在这里，我们展示了这些假设蛋白质的克隆、过表达和纯化。 Pcryo_0613 、 Pcryo_0