| 1402430-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1402430-21-0
• 化学式: C₁₄H₂₀N₄O₈
• 分子量: 372.335
• InChiKey: RCZQZPRGYCLVJZ-PDWCTOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  165.99
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-L-galactal 在 sodium azide 、 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 (2S,3S,4S,5S)-2-(acetoxymethyl)-5-azido-6-(nitrooxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 、
  参考文献：
  名称：

  Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: Syntheses and biological evaluations

  摘要：

  12-O-beta-D-glucopyranosyl jasmonic acid (JAG) shows unique biological activities, including leaf-closing of Samanea saman. It is expected that the mode of action for such regulation is distinct from that of other jasmonates. We developed high-performance compact molecular probes (CMPs) based on JAG that can be used for the FLAG-tagging of JAG target. We synthesized four hybrid-type JAG-CMP stereoisomers (7, ent-7, 8, and ent-8), which are composed of (-)-12-OH-JA (2)/D-galactopyranoside, (-)-2/L-galactopyranoside, (+)-ent-2/D-galactopyranoside, and (+)-ent-2/L-galactopyranoside moieties, respectively, and we examined their biological features, such as the stereospecific induction of shrinkage, rate of the cellular response, and dependence on potassium channel activity. These features of the JAG-CMPs were completely consistent with those of the original JAG. These results indicate the biological equivalence of JAG and the JAG-CMPs. During the course of such biological evaluations, it was revealed that the biological activity of the CMPs is greatly dependent on the D/L-stereochemistry of a glycon moiety. To the best of our knowledge, this is the first study suggesting that the D/L-stereochemistry of the glycon moiety significantly affects the biological activity of the associated glycoside. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.003