mappain

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: mappain
• 英文别名: 5-[(E)-2-[3,5-dihydroxy-4-(3-methylbut-2-enyl)phenyl]ethenyl]-3-[(2E)-3,7-dimethylocta-2,6-dienyl]benzene-1,2-diol
• 化学式: C₂₉H₃₆O₄
• 分子量: 448.602
• InChiKey: GJZKDVGLDGLPMB-ZVBRSKEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  mappain 在 Shi's ketone 、 双氧水 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 11.17h， 生成 (2R,4aR,9aR)-tri(O-methoxymethyl)schweinfurthin G
  参考文献：
  名称：

  WO2023/275324

  摘要：

  公开号：
• 作为产物：
  描述：

  5-{(E)-2-[3,5-bis(methoxymethoxy)-4-(3-methylbut-2-en-1-yl)phenyl]ethenyl}-1-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,3-bis(methoxymethoxy)benzene 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以62%的产率得到mappain
  参考文献：
  名称：

  首次将异戊二烯基和壬二烯基二苯乙烯合成马帕汀

  摘要：

  天然生成的mappain的第一个全合成已通过收敛序列实现。合成Mappain的关键策略是Horner – Wadsworth – Emmons通过相应的炔丙基苯甲醛与Geranylated苄基膦酸酯的（E）-形成。

  DOI：

  10.1002/hlca.200900318

文献信息

• Stilbenoid prenyltransferases from plants
  申请人：Arkansas State University—Jonesboro

  公开号：US10704052B2

  公开（公告）日：2020-07-07

  The process and system led to the identification of prenyltransferase genes from elicitor-treated peanut hairy roots. One of the prenyltransferases, AhR4DT-1 catalyzes a key reaction involved in the biosynthesis of prenylated stilbenoids, in which resveratrol is prenylated at its C-4 position to form arachidin-2, while another, AhR3′DT-1, was able to add the prenyl group to C-3′ of resveratrol. Each of these prenyltransferases has a high specificity for stilbenoid substrates, and their subcellular location in the plastid was confirmed by fluorescence microscopy. Structure analysis of the prenylated stilbenoids suggest that these two prenyltransferase activities represent the first committed steps in the biosynthesis of a large number of prenylated stilbenoids and their derivatives in peanut.

  通过这一过程和系统，从诱导剂处理过的花生毛根中鉴定出了前酰转移酶基因。其中一个前酰基转移酶（AhR4DT-1）催化了参与前酰基化二苯乙烯类化合物生物合成的一个关键反应，在该反应中，白藜芦醇在其 C-4 位置被前酰基化，形成花生苷-2；而另一个前酰基转移酶（AhR3′DT-1）能够将前酰基添加到白藜芦醇的 C-3′ 位置。这些前酰基转移酶对白藜芦醇底物都有很高的特异性，荧光显微镜证实了它们在质体中的亚细胞位置。前炔基化二苯乙烯类化合物的结构分析表明，这两种前炔基化转移酶活性代表了花生中大量前炔基化二苯乙烯类化合物及其衍生物生物合成的第一步。
• STILBENOID PRENYLTRANSFERASES FROM PLANTS
  申请人：Arkansas State University-Jonesboro

  公开号：EP3472309A2

  公开（公告）日：2019-04-24
• [EN] STILBENOID PRENYLTRANSFERASES FROM PLANTS<br/>[FR] PRÉNYLTRANSFÉRASES STILBÉNOÏDES PROVENANT DE PLANTES
  申请人：ARKANSAS STATE UNIV - JONESBORO

  公开号：WO2017218967A2

  公开（公告）日：2017-12-21

  The process and system led to the identification of prenyltransferase genes from elicitor- treated peanut hairy roots. One of the prenyltransferases, AhR4DT-1 catalyzes a key reaction involved in the biosynthesis of prenylated stilbenoids, in which resveratrol is prenylated at its C- 4 position to form arachidin-2, while another, AhR3'DT-1, was able to add the prenyl group to C-3' of resveratrol. Each of these prenyltransferases has a high specificity for stilbenoid substrates, and their subcellular location in the plastid was confirmed by fluorescence microscopy. Structure analysis of the prenylated stilbenoids suggest that these two prenyltransferase activities represent the first committed steps in the biosynthesis of a large number of prenylated stilbenoids and their derivatives in peanut.
• First Total Synthesis of Mappain with a Prenylated and Geranylated Stilbene
  作者：Lakkoju Chakrapani、Eun Mi Jung、Yong Rok Lee

  DOI：10.1002/hlca.200900318

  日期：2010.5

  The first total synthesis of naturally occurring mappain has been achieved by a convergent sequence. The key strategy involved in the synthesis of mappain was a (E)‐stilbene formation by Horner–Wadsworth–Emmons reaction of the corresponding prenylated benzaldehyde with a geranylated benzyl phosphonate.

  天然生成的mappain的第一个全合成已通过收敛序列实现。合成Mappain的关键策略是Horner – Wadsworth – Emmons通过相应的炔丙基苯甲醛与Geranylated苄基膦酸酯的（E）-形成。
• WO2023/275324
  申请人：——

  公开号：——

  公开（公告）日：——