methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-galacto-oct-7-enopyranoside | 1401562-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-galacto-oct-7-enopyranoside
• 英文别名: (1R)-1-[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]prop-2-en-1-ol
• CAS: 1401562-76-2
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: ROJJHGZTXDZFQU-FBLDLFPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-galacto-oct-7-enopyranoside 在 吡啶 、 甲基磺酰胺 、 hydroquinine 1,4-phthalazinediyl diether 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 生成 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-erythro-D-galacto-octopyranoside
  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
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 咪唑 、 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.58h， 生成 methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D-glycero-α-D-galacto-oct-7-enopyranoside 、 methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-L-glycero-α-D-galacto-oct-7-enopyranoside
  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

文献信息

• Construction of the Octose 8-Phosphate Intermediate in Lincomycin A Biosynthesis: Characterization of the Reactions Catalyzed by LmbR and LmbN
  作者：Eita Sasaki、Chia-I Lin、Ke-Yi Lin、Hung-wen Liu

  DOI：10.1021/ja308221z

  日期：2012.10.24

  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.