(+)-berbamunine | 485-18-7

• 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: (+)-berbamunine
• 英文别名: berbamunine；6,6'-dimethoxy-2,2'-dimethyl-8,18'-seco-berbamane-7,12-diol；6,6'-Dimethoxy-2,2'-dimethyl-8,18'-seco-berbaman-7,12-diol；(1S)-1-[[4-[2-hydroxy-5-[[(1R)-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]phenoxy]phenyl]methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
• CAS: 485-18-7
• 化学式: C₃₆H₄₀N₂O₆
• 分子量: 596.723
• InChiKey: FDABVSXGAMFQQH-XZWHSSHBSA-N

物化性质

• 沸点：
  738.3±60.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)
• 熔点：
  190-191 °C

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.9
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2S)-2-amino-3-(4-hydroxy(1,2,3,4,5,6-14C6)cyclohexa-1,3,5-trien-1-yl)propanoic acid 生成 (+)-berbamunine
  参考文献：
  名称：

  STADLER, RICHARD;LOEFFLER, SUSANNE;CASSELS, BRUCE K.;ZENK, MEINHART H., PHYTOCHEMISTRY, 27,(1988) N 8, C. 2557-2565

  摘要：

  DOI：

文献信息

• Phenol oxidative coupling of benzylisoquinoline alkaloids is catalysed by regio- and stereo-selective cytochrome P-450 linked plant enzymes: salutaridine and berbamunine
  作者：Meinhart H. Zenk、Roswitha Gerardy、Richard Stadler

  DOI：10.1039/c39890001725

  日期：——

  The alkaloids salutaridine and berbamunine are formed by intramolecular C–C and intermolecular C–O coupling, respectively, catalysed by cytochrome P-450 linked NADPH and O2 dependent microsomal bound plant specific enzymes.

  生物碱salutaridine和berbamunine由分子内C–C和分子间C–O偶联形成，分别由细胞色素P-450连接的NADPH和O 2依赖性微粒体结合的植物特异性酶催化。
• Compositions and methods for producing benzylisoquinoline alkaloids
  申请人：California Institute of Technology

  公开号：US10240176B2

  公开（公告）日：2019-03-26

  The present invention relates to host cells that produce compounds that are characterized as benzylisoquinolines, as well as select precursors and intermediates thereof. The host cells comprise one, two or more heterologous coding sequences wherein each of the heterologous coding sequences encodes an enzyme involved in the metabolic pathway of a benzylisoquinoline, or its precursors or intermediates from a starting compound. The invention also relates to methods of producing the benzylisoquinoline, as well as select precursors and intermediates thereof by culturing the host cells under culture conditions that promote expression of the enzymes that produce the benzylisoquinoline or precursors or intermediates thereof.

  本发明涉及可产生苄基异喹啉类化合物及其特定前体和中间体的宿主细胞。宿主细胞包括一个、两个或多个异源编码序列，其中每个异源编码序列编码一种酶，该酶参与从起始化合物到苄基异喹啉或其前体或中间体的代谢途径。本发明还涉及在促进产生苄基异喹啉或其前体或中间体的酶的表达的培养条件下培养宿主细胞，从而生产苄基异喹啉及其精选前体和中间体的方法。
• Engineered benzylisoquinoline alkaloid epimerases and methods of producing benzylisoquinoline alkaloids
  申请人：Antheia, Inc.

  公开号：US10544420B2

  公开（公告）日：2020-01-28

  The present disclosure provides systems and methods for increasing production of an alkaloid product through the epimerization of a (S)-1-benzylisoquinoline alkaloid to a (R)-1-benyzlisoquinoline alkaloid via an engineered epimerase in an engineered host cell. A (S)-1-benzylisoquinoline alkaloid is contacted with said engineered epimerase. Contacting said (S)-1-benzylisoquinoline alkaloid with said engineered epimerase converts said (S)-1-benzylisoquinoline alkaloid to said (R)-1-benzylisoquinoline alkaloid.

  本公开提供了通过工程宿主细胞中的工程表聚酶将(S)-1-苄基异喹啉生物碱表聚为(R)-1-苄基异喹啉生物碱来提高生物碱产品产量的系统和方法。将(S)-1-苄基异喹啉生物碱与所述工程表聚酶接触。将所述(S)-1-苄基异喹啉生物碱与所述工程表聚酶接触，将所述(S)-1-苄基异喹啉生物碱转化为所述(R)-1-苄基异喹啉生物碱。
• Methods of producing nor-opioid and nal-opioid benzylisoquinoline alkaloids
  申请人：Antheia, Inc.

  公开号：US10738335B2

  公开（公告）日：2020-08-11

  A method of demethylizing an opioid to a nor-opioid is provided. The method comprises contacting an opioid with at least one enzyme. Contacting the opioid with the at least one enzyme converts the opioid to a nor-opioid. A method of converting a nor-opioid to a nal-opioid is provided. The method comprises contacting a nor-opioid with at least one enzyme. Contacting the nor-opioid with the at least one enzyme converts the nor-opioid to a nal-opioid.

  本发明提供了一种将阿片类药物去甲基化为非阿片类药物的方法。该方法包括将阿片类药物与至少一种酶接触。将阿片与至少一种酶接触可将阿片转化为去甲阿片。提供了一种将去甲阿片转化为正阿片的方法。该方法包括将去甲阿片与至少一种酶接触。将去甲阿片与至少一种酶接触可将去甲阿片转化为正阿片。
• Benzylisoquinoline alkaloid (BIA) precursor producing microbes, and methods of making and using the same
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US10752903B2

  公开（公告）日：2020-08-25

  Methods and engineered yeast cells for generating a benzylisoquinoline alkaloid product are provided herein. A method comprises providing engineered yeast cells and a feedstock to a reactor. In the reactor, the engineered yeast cells are subjected to fermentation by incubating the engineered yeast cells for a time period to produce a solution comprising the BIA product and cellular material. The solution comprises not more than one class of molecule selected from the group of protoberberine, morphinan, isopavine, aporphine, and benzylisoquinoline. Additionally, at least one separation unit is used to separate the BIA product from the cellular material to provide the product stream comprising the BIA product.

  本文提供了生成苄基异喹啉生物碱产品的方法和工程酵母细胞。一种方法包括向反应器提供工程酵母菌细胞和原料。在反应器中，通过培养工程酵母菌细胞一段时间，使工程酵母菌细胞进行发酵，以产生一种包含苄基异喹啉生物碱产品和细胞材料的溶液。该溶液包含不多于一种选自原小檗碱、吗啡烷、异小檗碱、卟吩和苄基异喹啉组的分子。此外，至少一个分离装置用于将 BIA 产物从细胞材料中分离出来，以提供包含 BIA 产物的产品流。