Salutaridinol I | 2392-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Salutaridinol I
• 英文别名: (7R)-salutaridinol；(1S,9R,12R)-4,13-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10,13-pentaene-3,12-diol
• CAS: 2392-98-5
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: LLSADFZHWMEBHH-LPMFXHHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Salutaridinol I 在 氢气 作用下， 生成 蒂巴因
  参考文献：
  名称：

  吗啡生物合成中氧化桥的关闭

  摘要：

  已经发现了高度底物特异性的酶并将其纯化至均质，其将乙酰基部分从乙酰辅酶A转移至salutaridinol的7-OH基团。形成的7-O-乙酰基-芦丁氨醇自发地通过烯丙基消除作用关闭吗啡前体蒂巴因的氧化桥。

  DOI：

  10.1016/s0040-4039(00)76696-2

文献信息

• Salutaridine reductase and morphine biosynthesis
  申请人：Leibniz-Institut für Pflanzenbiochemie (IPB)

  公开号：EP1837396A1

  公开（公告）日：2007-09-26

  Plants of the order Ranunculales, especially members of the species Papaver, accumulate a large variety of benzylisoquinoline alkaloids with about 2,500 structures. But only the opium poppy, Papaver somniferum, and Papaver setigerum, are able to produce morphinan alkaloids such as the analgesic morphine or the antitussive codeine. We investigated the molecular basis for this exceptional biosynthetic capability by comparison of alkaloid profiles with gene expression profiles between sixteen different Papaver species and identified one cDNA which exhibits very similar expression pattern to previously isolated cDNAs coding for enzymes in benzylisoquinoline biosynthesis and which showed the highest amino acid identity to reductases in menthol biosynthesis. When expressed, the protein encoded by this cDNA reduced the keto group of salutaridine yielding salutaridinol, an intermediate in morphine biosynthesis. The stereoisomer epi-salutaridinol was not formed. The encoded protein was identified as salutaridine reductase (SalR; EC 1.1.1.248) and it was found to belongs to the family of the short chain dehydrogenases / reductases.

  毛茛目植物，尤其是罂粟属物种，积累了大量的苯基异喹啉生物碱，约有2500种结构。但只有鸦片罂粟（Papaver somniferum）和刺毛罂粟（Papaver setigerum）等品种能够产生吗啡等镇痛药物吗啡类生物碱或镇咳药可待因。我们通过比较16种不同罂粟属植物的生物碱谱与基因表达谱，鉴定出一个cDNA，其表达模式与之前分离的编码苯基异喹啉生物合成酶的cDNA非常相似，并且与薄荷醇生物合成中的还原酶具有最高的氨基酸同源性。当表达时，这个cDNA编码的蛋白质将沙洛特啶的酮基还原为沙洛特啉醇，这是吗啡生物合成中的中间体。而对映异构体外沙洛特啉醇并未形成。这个编码的蛋白质被鉴定为沙洛特啶还原酶（SalR；EC 1.1.1.248），并且发现它属于短链脱氢酶/还原酶家族。
• Compositions and methods for making benzylisoquinoline alkaloids, morphinan alkaloids, thebaine, and derivatives thereof
  申请人：Antheia, Inc.

  公开号：US11142780B2

  公开（公告）日：2021-10-12

  Disclosed herein are methods that may be used for the synthesis of benzylisoquinoline alkaloids (BIAs) such as alkaloid morphinan. The methods disclosed can be used to produce thebaine, oripavine, codeine, morphine, oxycodone, hydrocodone, oxymorphone, hydromorphone, naltrexone, naloxone, hydroxycodeinone, neopinone, and/or buprenorphine. Compositions and organisms useful for the synthesis of BIAs, including thebaine synthesis polypeptides, purine permeases, and polynucleotides encoding the same, are provided.

  本文公开了可用于合成苄基异喹啉生物碱（BIAs）（如生物碱吗啡南）的方法。所公开的方法可用于生产巴因、奥列巴因、可待因、吗啡、羟考酮、氢可酮、羟吗啡酮、氢吗啡酮、纳曲酮、纳洛酮、羟基可待因、新可待因和/或丁丙诺啡。提供了用于合成 BIAs 的组合物和生物体，包括生物碱合成多肽、嘌呤渗透酶和编码这些多肽的多核苷酸。
• MICROORGANISMS AND METHODS IN THE FERMENTATION OF BENZYLISOQUINOLINE ALKALOIDS
  申请人：Intrexon Corporation

  公开号：EP3678667A1

  公开（公告）日：2020-07-15
• COMPOSITIONS AND METHODS FOR MAKING BENZYLISOQUINOLINE ALKALOIDS, MORPHINAN ALKALOIDS, THEBAINE, AND DERIVATIVES THEREOF
  申请人：INTREXON CORPORATION

  公开号：US20200140906A1

  公开（公告）日：2020-05-07

  Disclosed herein are methods that may be used for the synthesis of benzylisoquinoline alkaloids (BIAs) such as alkaloid morphinan. The methods disclosed can be used to produce thebaine, oripavine, codeine, morphine, oxycodone, hydrocodone, oxymorphone, hydromorphone, naltrexone, naloxone, hydroxycodeinone, neopinone, and/or buprenorphine. Compositions and organisms useful for the synthesis of BIAs, including thebaine synthesis polypeptides, purine permeases, and polynucleotides encoding the same, are provided.
• Microorganisms and Methods in the Fermentation of Benzylisoquinoline Alkaloids
  申请人：Intrexon Corporation

  公开号：US20200325509A1

  公开（公告）日：2020-10-15

  Disclosed herein are methods that may be used for the synthesis of benzylisoquinoline alkaloids (“BIAs”) such as thebaine and morphine and their derivatives. The methods disclosed can be used to produce thebaine, oripavine, codeine, morphine, oxycodone, hydrocodone, oxymorphone, hydromorphone, naltrexone, naloxone, hydroxycodeinone, neopinone, and/or buprenorphine. Compositions and organisms useful for the synthesis of BIAs, including thebaine synthases and polynucleotides encoding the same, are provided. Further, methods of adjusting pH to optimize the reaction are disclosed.