coniferin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: coniferin
• 英文别名: (2S,3R,4S,5S,6R)-2-[2-hydroxy-4-[(E)-3-hydroxyprop-1-enyl]-6-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₆H₂₂O₉
• 分子量: 358.345
• InChiKey: IOHFXPMLJVIQRA-LRCHNLNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 5-hydroxyconiferyl alcohol 在 glycosyltransferase 72E₃ derived from Arabidopsis thaliana 、 2-巯基乙醇 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 生成 coniferin
  参考文献：
  名称：

  Enzymatic and metabolic engineering for efficient production of syringin, sinapyl alcohol 4-O-glucoside, in Arabidopsis thaliana

  摘要：

  To promote efficient production of syringin, a plant-derived bioactive monolignol glucoside, synergistic effects of enzymatic and metabolic engineering were combined. Recombinant UGT72E3IE2 chimeras, generated by exchanging parts of the C-terminal domain including the Putative Secondary Plant Glycosyltransferase (PSPG) motif of UGT72E3 and UGT72E2, were expressed in leaves of transgenic Arabidopsis plants; syringin production was measured in vivo and by enzymatic assays in vitro. In both tests, UGT72E3/2 displayed substrate specificity for sinapyl alcohol like the parental enzyme UGT72E3, and the syringin production was significantly increased compared to UGT72E3. In particular, in the in vitro assay, which was performed in the presence of a high concentration of sinapyl alcohol, the production of syringin by UGT72E3/2 was 4-fold higher than by UGT72E3. Furthermore, to enhance metabolic flow through the phenylpropanoid pathway and maintain a high basal concentration of sinapyl alcohol in the leaves, UGT72E3I2 was combined with the sinapyl alcohol synthesis pathway gene F5H encoding ferulate 5-hydroxylase and the lignin biosynthesis transcriptional activator MYB58. The resulting UGT72E3/2+F5H+MYB58 OE plants, which simultaneously overexpress these three genes, accumulated a 56-fold higher level of syringin in their leaves than wild-type plants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2014.03.003