(S)-N-methylcoclaurinium(1+)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (S)-N-methylcoclaurinium(1+)
• 英文别名: (1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-7-ol
• 化学式: C18H22NO3+
• 分子量: 300.4
• InChiKey: BOKVLBSSPUTWLV-INIZCTEOSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-methylcoclaurinium(1+) 、 氧气 、 1-Deoxy-1-(7,8-dimethyl-2,4-dioxidobenzo[g]pteridin-10(5H)-yl)-5-O-phosphonopentitol 生成 (S)-3'-hydroxy-N-methylcoclaurinium(1+) 、 氢(+1)阳离子 、 水 、 FMN
  参考文献：
  名称：

  Molecular cloning and functional heterologous expression of two alleles encoding (S)‐N‐methylcoclaurine 3′‐hydroxylase (CYP80B1), a new methyl jasmonate‐inducible cytochrome P‐450‐dependent mono‐oxygenase of benzylisoquinoline alkaloid biosynthesis

  摘要：

  SummaryAlkaloids derived from the tetrahydrobenzylisoquinoline alkaloid (S)‐N‐methylcoclaurine represent a vast and varied structural array of physiologically active molecules. These compounds range from the dimeric bisbenzylisoquinolines, such as the muscle relaxant (+)‐tubocurarine, to the powerful anaesthetic opiate morphine, the anti‐microbial berberine and the anti‐microbial benzo[c]phenanthridine sanguinarine. The 3′‐hydroxylation of (S)‐N‐methylcoclaurine is a branch point that is the penultimate step in the biosynthesis of the central alkaloidal intermediate (S)‐reticuline. This study identified this enzyme as a cytochrome P‐450‐dependent mono‐oxygenase that has until now eluded attempts at identification using in vitro enzyme assays. Two alleles encoding this new enzyme (S)‐N‐methylcoclaurine 3′‐hydroxylase (CYP80B1) were isolated from a cDNA library prepared from poly(A)+ RNA isolated from methyl jasmonate‐induced cell‐suspension cultures of the California poppy Eschscholzia californica. Partial clones generated by RT–PCR with cytochrome P‐450‐specific primers were used as hybridization probes. RNA gel‐blot hybridization indicated that the transcripts for CYP80B1 accumulate in response to the addition of methyl jasmonate to the cell culture medium. Both alleles were functionally expressed in Saccharomyces cerevisiae and in Spodoptera frugiperda Sf9 cells in the presence and absence of the E. californica cytochrome P‐450 reductase. The enzyme was found to hydroxylate exclusively (S)‐N‐methylcoclaurine with a pH optimum of 7.5, temperature optimum of 35°C and a Km of 15 μm. In addition to the CYP80B1 alleles, another cytochrome P‐450 with an inducible transcript (CYP82B1) was isolated and expressed in the same manner, but was not found to be involved in alkaloid biosynthesis in this plant.

  DOI：

  10.1046/j.1365-313x.1998.00085.x
• 作为产物：
  描述：

  (1S)-7-hydroxy-1-(4-hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolinium 、 S-腺苷蛋氨酸 生成 (S)-N-methylcoclaurinium(1+) 、 氢(+1)阳离子 、 S-(5'-腺苷)-L-高半胱氨酸
  参考文献：
  名称：

  黄连培养细胞中可乐碱N-甲基转移酶的分子克隆与鉴定。

  摘要：

  在异喹啉生物碱生物合成中，S-腺苷-L-蛋氨酸：可尿酸N-甲基转移酶（CNMT）将可尿酸转化为N-甲基可尿酸。Coptis CNMT的N端氨基酸序列用于扩增相应的cDNA片段，随后使用cDNA末端的5'和3'快速扩增（RACE）分离全长cDNA。核苷酸序列和预测的氨基酸序列表明，该cDNA编码了358个氨基酸，其中包含一个推定的S-腺苷-L-甲硫氨酸结合结构域，并且与番茄磷酸乙醇胺-N-甲基转移酶具有较高的同源性。重组蛋白在大肠杆菌中表达，并确认了其CNMT活性。重组CNMT纯化至均一，酶学鉴定证实黄连CNMT具有相当广泛的底物特异性，即 不仅适用于6-O-甲基去甲去甲去氧胆碱和去甲肾上腺素，而且还适用于6,7-二甲氧基-1,2,3,4-四氢异喹啉。基于序列相似性，讨论了次级代谢中N-甲基转移酶的进化。

  DOI：

  10.1074/jbc.m106405200

文献信息

• Stadler R.; Zenk M.H., J Biol Chem, 1993, 0021-9258, 823-31
  作者：Stadler R.、Zenk M.H.

  DOI：——

  日期：——