[O(14)CH3]-labelled vanillic acid | 100647-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [O(14)CH3]-labelled vanillic acid
• 英文别名: [O(14)CH3]-labelled 4-hydroxy-3-methoxy-benzoic acid；-Vanillinsaeure；Vanillinsaeure (O¹⁴CH3)；<3'-O-Methyl-14C>-veratrumsaeure；4-hydroxy-3-[¹⁴C]methoxy-benzoic acid；4-hydroxy-3-(114C)methoxybenzoic acid
• CAS: 100647-77-6
• 化学式: C₈H₈O₄
• 分子量: 170.138
• InChiKey: WKOLLVMJNQIZCI-NJFSPNSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  原儿茶酸 、 S-adenosyl-L-[Me-(14)C]methionine 在 5-O-methyltransferase 、 咖啡酸 、 5-羟基阿魏酸 作用下， 生成 [O(14)CH3]-labelled vanillic acid
  参考文献：
  名称：

  O-Methylation of benzaldehyde derivatives by “lignin specific” caffeic acid 3-O-methyltransferase

  摘要：

  Although S-adenOSyl-L-methionine (SAM) dependent caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase (COMT) is one of the key enzymes in lignin biosynthesis, the present work demonstrates that alfalfa COMT methylates benzaldehyde derivatives more efficiently than lignin pathway intermediates. 3,4-Dihydroxy, 5-methoxybenzaldehyde and protocatechuic aldehyde were the best in vitro substrates for OMT activity in extracts from developing alfalfa stems, and these compounds were preferred over lignin pathway intermediates for 3-O-methylation by recombinant alfalfa COMT expressed in Escherichia coli. OMT activity with benzaldehydes was strongly reduced in extracts from stems of transgenic alfalfa down-regulated in COMT. However, although COMT down-regulation drastically affects lignin composition, it does not appear to significantly impact metabolism of benzaldehyde derivatives in alfalfa. Structurally designed site-directed mutants of COMT showed altered relative substrate preferences for lignin precursors and benzaldehyde derivatives. Taken together, these results indicate that COMT may have more than one role in phenyl-propanoid metabolism (but probably not in alfalfa), and that engineered COMT enzymes could be useful for metabolic engineering of both lignin and benzaldehyde-derived flavors and fragrances. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.01.017