UDP-N-acetyl-alpha-D-quinovosamine

• 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-N-acetyl-alpha-D-quinovosamine
• 英文别名: [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-methyloxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] phosphate
• 化学式: C17H25N3O16P2-2
• 分子量: 589.3
• InChiKey: INJACODUUNZJCO-WNSRFTAOSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  286
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  NADP⁺ 、 UDP-N-acetyl-alpha-D-quinovosamine 生成 氢(+1)阳离子 、 NADPH(4-) 、 UDP-2-acetamido-2,6-dideoxy-alpha-D-xylo-hex-4-ulose(2-)
  参考文献：
  名称：

  UDP-N-乙酰基-d-奎诺糖胺（UDP-d-QuiNAc）的体外生物合成和化学鉴定。

  摘要：

  N-乙酰基-d-喹诺糖胺（2-乙酰氨基-2,6-双脱氧-d-葡萄糖，QuiNAc）存在于许多革兰氏阴性菌的多糖结构中。在含有 QuiNAc 的多糖的生物合成中，UDP-QuiNAc 是 QuiNAc 残基的假设供体。UDP-QuiNAc 的生物合成已被提议通过 UDP-N-乙酰基-d-葡糖胺 (UDP-GlcNAc) 的 4,6-脱水生成 UDP-2-acetamido-2,6-dideoxy-d-xylo-4-己酮糖，然后将此 4-酮中间体还原为 UDP-QuiNAc。已知几种特定的脱水酶可催化第一个提出的步骤。最后一步的特定还原酶尚未在体外得到证实，但先前的突变分析表明根瘤菌 etli 基因 wreQ 可能编码这种还原酶。因此，该基因被克隆并在大肠杆菌中表达，纯化得到的带有 His6 标签的 WreQ 蛋白。通过将其和 NAD(P)H 添加到反应混合物中来测试 4-还原酶活性，其中 4

  DOI：

  10.1074/jbc.m114.555862

文献信息

• Genetic Locus and Structural Characterization of the Biochemical Defect in the O-Antigenic Polysaccharide of the Symbiotically Deficient Rhizobium etli Mutant, CE166
  作者：L. Scott Forsberg、K. Dale Noel、Jodie Box、Russell W. Carlson

  DOI：10.1074/jbc.m309016200

  日期：2003.12

  The O-antigen polysaccharide (OPS) of Rhizobium etli CE3 lipopolysaccharide (LPS) is linked to the core oligosaccharide via an N-acetylquinovosaminosyl (QuiNAc) residue. A mutant of CE3, CE166, produces LPS with reduced amounts of OPS, and a suppressed mutant, CE166alpha, produces LPS with nearly normal OPS levels. Both mutants are deficient in QuiNAc production. Characterization of OPS from CE166 and CE166alpha showed that QuiNAc was replaced by its 4-keto derivative, 2-acetamido-2,6-dideoxyhexosyl-4-ulose. The identity of this residue was determined by NMR and mass spectrometry, and by gas chromatography-mass spectrometry analysis of its 2-acetamido-4-deutero-2,6-dideoxyhexosyl derivatives produced by reduction of the 4-keto group using borodeuteride. Mass spectrometric and methylation analyses showed that the 2-acetamido-2,6-dideoxyhexosyl-4-ulosyl residue was 3-linked and attached to the core-region external Kdo III residue of the LPS, the same position as that of QuiNAc in the CE3 LPS. DNA sequencing revealed that the transposon insertion in strain CE166 was located in an open reading frame whose predicted translation product, LpsQ, falls within a large family of predicted open reading frames, which includes biochemically characterized members that are sugar epimerases and/or reductases. A hypothesis to be tested in future work is that lpsQ encodes UDP-2-acetamido-2,6-dideoxyhexosyl-4-ulose reductase, the second step in the synthesis of UDP-QuiNAc from UDP-GlcNAc.
• In Vitro Biosynthesis and Chemical Identification of UDP-N-acetyl-d-quinovosamine (UDP-d-QuiNAc)
  作者：Tiezheng Li、Laurie Simonds、Evgenii L. Kovrigin、K. Dale Noel

  DOI：10.1074/jbc.m114.555862

  日期：2014.6

  NADH led to formation of a third compound. Combined gas chromatography-mass spectrometry analysis of acid hydrolysates of the final reaction mixture showed that a quinovosamine moiety had been synthesized after WreQ addition. The two-step reaction progress also was monitored in real time by NMR. The final UDP-sugar product after WreQ addition was purified and determined to be UDP-d-QuiNAc by one-dimensional

  N-乙酰基-d-喹诺糖胺（2-乙酰氨基-2,6-双脱氧-d-葡萄糖，QuiNAc）存在于许多革兰氏阴性菌的多糖结构中。在含有 QuiNAc 的多糖的生物合成中，UDP-QuiNAc 是 QuiNAc 残基的假设供体。UDP-QuiNAc 的生物合成已被提议通过 UDP-N-乙酰基-d-葡糖胺 (UDP-GlcNAc) 的 4,6-脱水生成 UDP-2-acetamido-2,6-dideoxy-d-xylo-4-己酮糖，然后将此 4-酮中间体还原为 UDP-QuiNAc。已知几种特定的脱水酶可催化第一个提出的步骤。最后一步的特定还原酶尚未在体外得到证实，但先前的突变分析表明根瘤菌 etli 基因 wreQ 可能编码这种还原酶。因此，该基因被克隆并在大肠杆菌中表达，纯化得到的带有 His6 标签的 WreQ 蛋白。通过将其和 NAD(P)H 添加到反应混合物中来测试 4-还原酶活性，其中 4