3-deoxy-8-O-phosphono-alpha-D-manno-oct-2-ulopyranosonic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-8-O-phosphono-alpha-D-manno-oct-2-ulopyranosonic acid
• 英文别名: (2R,4R,5R,6R)-2,4,5-trihydroxy-6-[(1R)-1-hydroxy-2-phosphonooxyethyl]oxane-2-carboxylic acid
• 化学式: C₈H₁₅O₁₁P
• 分子量: 318.174
• InChiKey: IZZNRKJLBIYBJN-HXUQBWEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  194
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2,3,4-三羟基-5-氧代戊基)磷酸二氢酯 、 磷烯醇丙酮酸 在 DAH 7-P synthase 、 Tris buffer 、 manganese(ll) chloride 作用下， 以 水 为溶剂， 反应 0.17h， 以60%的产率得到3-deoxy-8-O-phosphono-alpha-D-manno-oct-2-ulopyranosonic acid
  参考文献：
  名称：

  Enzymatic Synthesis of 3-Deoxy-d-manno-octulosonate 8-Phosphate, 3-Deoxy-d-altro-octulosonate 8-Phosphate, 3,5-Dideoxy-d-gluco(manno)-octulosonate 8-Phosphate by 3-Deoxy-d-arabino-heptulosonate 7-Phosphate Synthase

  摘要：

  The phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAH 7-P) synthase (phe), a key enzyme involved in the biosynthesis of the aromatic amino acid phenylalanine, expressed by the Escherichia coli gene aroG, which catalyzes the condensation of D-erythrose 4-phosphate with phosphoenolpyruvate (PEP) to give DAH 7-P, was cloned into the expression vector pT7-7 for overexpression in E. coli. Purified enzyme from this expression system was used to demonstrate that DAH 7-P synthase (phe) also catalyses the aldol-type condensation of PEP with the 5-carbon analogues D-arabinose 5-phosphate, D-ribose 5-phosphate, and 2-deoxy-D-ribose 5-phosphate to yield 3-deoxy-D-manno-octulosonate 8-phosphate, 3-deoxy-D-altro-octulosonate 8-phosphate, and 3,5-dideoxy-D-gluco(manno)-octulosonate 8-phosphate, respectively, as determined by H-1 NMR and other standard analytical methods. The kinetic parameters, K-m and V-max, for these reactions were determined. The 3- and 6-carbon phosphorylated monosaccharides, D,L-glyceraldehyde 3-phosphate and D-glucose 6-phosphate, as well as the nonphosphorylated 5-carbon analogues D-arabinose 5-phosphate, D-ribose 5-phosphate, and 2-deoxy-D-ribose 5-phosphate were not substrates.

  DOI：

  10.1021/ja9816281