(-)-Ephedrinium

• 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: (-)-Ephedrinium
• 英文别名: [(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-methylazanium
• 化学式: C10H16NO+
• 分子量: 166.24
• InChiKey: KWGRBVOPPLSCSI-WPRPVWTQSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-Ephedrinium 、 nicotinamide adenine dinucleotide 生成 (S)-N-methylcathinone 、 氢(+1)阳离子 、 NADH
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Regeneration of 6-fluoro-4-chromanone from
  申请人：Pfizer Inc.

  公开号：US04551542A1

  公开（公告）日：1985-11-05

  6-Fluoro-4-chromanone can be regenerated from (R)-6-fluoro-4-ureidochroman-4-carboxylic acid, or from mixtures of (R)-6-fluoro-4-ureidochroman-4-carboxylic acid and its racemic modification, by oxidation with a permanganate, especially potassium permanganate. 6-Fluoro-4-chromanone is a chemical intermediate useful for preparing sorbinil, an aldose reductase inhibitor which can be used in clinical medicine for the control of the chronic complications of diabetes. (R)-6-Fluoro-4-ureidochroman-4-carboxylic acid and its racemic modification are by-products from the production of sorbinil from 6-fluoro-4-chromanone.

  6-氟-4-香豆酮可以通过过氧化钾，特别是高锰酸钾的氧化作用，从(R)-6-氟-4-尿素基香豆酸或(R)-6-氟-4-尿素基香豆酸和其外消旋异构体的混合物中再生。6-氟-4-香豆酮是一种化学中间体，用于制备索比尼尔，一种醛糖还原酶抑制剂，可用于临床医学中控制糖尿病的慢性并发症。(R)-6-氟-4-尿素基香豆酸及其外消旋异构体是从6-氟-4-香豆酮制备索比尼尔的副产物。
• Degradation of (–)-Ephedrine by Pseudomonas putida Detection of (–)-Ephedrine: NAD⁺-oxidoreductase from Arthrobacter globiformis
  作者：E. Klamann、F. Lingens

  DOI：10.1515/znc-1980-1-216

  日期：1980.2.1

  A bacterium utilizing the alkaloid (-)-ephedrine as its sole source of carbon was isolated by an enrichment-culture technique from soil supplemented with 4-benzoyl-1,3-oxazolidinon-(2). The bacterium was identified as Pseudomonasputida by morphological and physiological studies. The following metabolites were isolated from the culture fluid: methylamine, formaldehyde, methyl- benzoylcarbinol (2-hydroxy-1-oxo-1-phenylpropane), benzoid acid, pyrocatechol and cis, cis- muconic acid. A pathway for the degradation of (-)-ephedrine by Pseudomonas putida is proposed and compared with the degradative pathway in Arthrobacter globiformis.

  The enzyme, which is responsible for the first step in the catabolism of (-)-ephedrine could be demonstrated in extracts from Arthrobacter globiformis. This enzyme catalyses the dehydrogena- tion of (-)-ephedrine yielding phenylacetylcarbinol/methylbenzoylcarbinol and methylamine. It requires NAD⁺ as cofactor and exhibits optimal activity at pH 11 in 0.1 m glycine/NaOH buffer. The K_m value for (-)-ephedrine is 0.02 mM and for NAD⁺ 0.11 mм, respectively. No remarkable loss of activity is observed following treatment with EDTA. The enzyme has been shown to react with a wide range of ethanolamines. A slight enrichment was obtained by ammonium sulphate precipitation. The name (-)-ephedrine: NAD⁺-oxidoreductase (deaminating) is proposed.

  标题：摘要 一株利用生物碱（-）-麻黄碱作为唯一碳源的细菌，通过富集培养技术从添加了4-苯甲酰-1,3-噁唑啉（2）的土壤中分离得到。通过形态学和生理学研究，确定了这种细菌为假单胞菌。从培养液中分离出以下代谢产物：甲胺，甲醛，甲基苯甲酰丙酮（2-羟基-1-氧代-1-苯基丙烷），苯甲酸，间苯二酚和顺式、顺式-顺二羧酸。提出了假单胞菌降解（-）-麻黄碱的途径，并与球形芽孢杆菌的降解途径进行了比较。 从球形芽孢杆菌的提取物中证明了负责（-）-麻黄碱分解的第一步的酶。该酶催化（-）-麻黄碱的脱氢反应，产生苯乙酰丙酮/甲基苯甲酰丙酮和甲胺。它需要NAD⁺作为辅酶，在0.1 m甘氨酸/NaOH缓冲液中的pH 11下表现出最佳活性。(-)-麻黄碱的K_m值为0.02 mM，NAD⁺的K_m值为0.11 mм。处理EDTA后没有观察到显著的活性损失。该酶已被证明可以与广泛的乙醇胺反应。通过硫酸铵沉淀获得了轻微的富集。提出了(-)-麻黄碱：NAD⁺氧化还原酶（脱氨）的名称。