伏格列波糖杂质9 | 1384518-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 伏格列波糖杂质9
• 英文名称: 2-epi-valiolone
• 英文别名: 2-epi-Valiolone；(2S,3S,4S,5S)-2,3,4,5-tetrahydroxy-5-(hydroxymethyl)cyclohexan-1-one
• CAS: 1384518-63-1
• 化学式: C₇H₁₂O₆
• 分子量: 192.169
• InChiKey: JCZFNXYQGNLHDQ-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2,3,4,5,7-五羟基-6-氧代庚基)磷酸二氢酯 在 purine nucleoside phosphorilase 、 β-烟酰胺腺嘌呤二核苷酸 、 cobalt(II) chloride 作用下， 生成 伏格列波糖杂质9
  参考文献：
  名称：

  Evolutionary Divergence of Sedoheptulose 7-Phosphate Cyclases Leads to Several Distinct Cyclic Products

  摘要：

  Sedoheptulose 7-phosphate cyclases are enzymes that utilize the pentose phosphate pathway intermediate,. sedoheptulose 7-phosphate, to generate cyclic precursors of many bioactive natural products, such as the antidiabetic drug acarbose, the crop protectant validamycin, and the natural sunscreens mycosporine-like amino acids. These proteins are phylogenetically related to the dehydroquinate (DHQ) synthases from the shikimate pathway and are part of the more recently recognized superfamily of sugar phosphate cyclases, which includes DHQ synthases, aminoDHQ synthases, and 2-deoxy-scyllo-inosose synthases. Through genome mining and biochemical studies, we identified yet another subset of DHQS-like proteins in the actinomycete Actinosynnema mirum and the myxobacterium Stigmatella aurantiaca DW4/3-1. These enzymes catalyze the conversion of sedoheptulose 7-phosphate to 2-epi-valiolone, which is predicted to be an alternative precursor for aminocyclitol biosynthesis. Comparative bioinformatics and biochemical analyses of these proteins with 2-epi-5-epi-valiolone synthases (EEVS) and desmethyl-4-deoxygadusol synthases (DDGS) provided further insights into their genetic diversity, conserved amino acid sequences, and plausible catalytic mechanisms. The results further highlight the uniquely diverse DHQS-like sugar phosphate cyclases, which may provide new tools for chemoenzymatic, stereospecific synthesis of various cyclic molecules.

  DOI：

  10.1021/ja3041866