2-脱氧-alpha-L-赤式戊呋喃糖 | 113890-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-脱氧-alpha-L-赤式戊呋喃糖
• 英文名称: 2-deoxy-L-ribose
• 英文别名: 2-Deoxy-alpha-L-erythro-pentofuranose；(2R,4R,5S)-5-(hydroxymethyl)oxolane-2,4-diol
• CAS: 113890-35-0
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: PDWIQYODPROSQH-MROZADKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-脱氧-alpha-L-赤式戊呋喃糖 在 甲烷磺酸 、 4-二甲氨基吡啶 作用下， 生成 methyl 2-deoxy-α-L-erythro-pentofuranoside
  参考文献：
  名称：

  Methods of manufacture of 2'-deoxy-beta-L-nucleosides

  摘要：

  本发明涉及2'-脱氧-β-L-胸苷、2'-脱氧-β-L-尿苷和2'-脱氧-β-L-胞苷的合成，以及它们的衍生物，如3'-O-酰基或3',5'-O-二酰基前药，包括3'-O-L-氨基酰和3',5'-O-L-二氨基酰前药，特别是3'-O-L-缬氨酰和3',5'-O-L-二缬氨酰前药。

  公开号：

  US20040266996A1
• 作为产物：
  描述：

  (2RS,3SR)-hex-5-ene-1,2,3-triol 在 甲醇 、 臭氧 作用下， 反应 0.5h， 生成 2-脱氧-alpha-L-赤式吡喃糖 、 2-脱氧-beta-L-赤式戊呋喃糖 、 2-脱氧-alpha-L-赤式戊呋喃糖 、 2-脱氧-D-阿拉伯吡喃糖
  参考文献：
  名称：

  Synthesis of sn-1 functionalized phospholipids as substrates for secretory phospholipase A2

  摘要：

  Secretory phospholipase A2 (sPLA2) represents a family of small water-soluble enzymes that catalyze the hydrolysis of phospholipids in the sn-2 position liberating free fatty acids and lysophospholipids. Herein we report the synthesis of two new phospholipids (1 and 2) with bulky allyl-substituents attached to the sn-1 position of the glycerol backbone. The synthesis of phospholipids 1 and 2 is based upon the construction of a key aldehyde intermediate 3 which locks the stereochemistry in the sn-2 position of the final phospholipids. The aldehyde functionality serves as the site for insertion of the allyl-substituents by a zinc mediated allylation. Small unilamellar liposomes composed of phospholipids 1 and 2 were subjected to sPLA2 activity measurements. Our results show that only phospholipid 1 is hydrolyzed by the enzyme. Molecular dynamics simulations revealed that the lack of hydrolysis of phospholipid 2 is due to steric hindrance caused by the bulky side chain of the substrate allowing only limited access of water molecules to the active site.

  DOI：

  10.1016/j.chemphyslip.2006.12.006