1,2,3,4,6,7,8-hepta-O-acetyl-α,β-D-erythro-D-gluco-octopyranose | 1401562-67-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4,6,7,8-hepta-O-acetyl-α,β-D-erythro-D-gluco-octopyranose
• CAS: 1401562-67-1
• 化学式: C₂₂H₃₀O₁₅
• 分子量: 534.471
• InChiKey: CHEKRFJRENURJB-CBDMQDTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  193.33
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-gluco-oct-7-enopyranoside 在 吡啶 、 甲基磺酰胺 、 hydroquinine 1,4-phthalazinediyl diether 、 硫酸 、 5%-palladium/activated carbon 、 氢气 、 乙酸酐 作用下， 以 甲醇 、 水 、 溶剂黄146 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 80.0h， 生成 1,2,3,4,6,7,8-hepta-O-acetyl-α,β-D-erythro-D-gluco-octopyranose
  参考文献：
  名称：

  Construction of the Octose 8-Phosphate Intermediate in Lincomycin A Biosynthesis: Characterization of the Reactions Catalyzed by LmbR and LmbN

  摘要：

  Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C-8-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of D-erythro-D-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using D-fructose 6-phosphate or D-sedoheptulose 7-phosphate as the C-3 donor and D-ribose 5-phosphate as the C-5 acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C-8-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C-8 backbone of MTL.

  DOI：

  10.1021/ja308221z