鏈菌鹼 | 7229-50-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 鏈菌鹼
• 中文别名: 链菌碱
• 英文名称: (2S)-2-[(2S,4Z)-4-[(2E,4E,6R)-6-[(1S,2S,3S,5S,6S)-2,5-dimethylspiro[4,9-dioxabicyclo[3.3.1]non-7-ene-6,2'-oxirane]-3-yl]-1-hydroxy-4-methyl-hepta-2,4-dienylidene]-1-[(2S,5S,6S)-5-hydroxy-6-methyl-tetrahydropyran-2-yl]-3,5-dioxo-pyrrolidin-2-yl]-N-methyl-propanamide
• 英文别名: (2S)-2-[(2S,4Z)-4-[(2E,4E,6R)-6-[(1S,3S,4S,5S,8S)-1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2'-oxirane]-3-yl]-1-hydroxy-4-methylhepta-2,4-dienylidene]-1-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide
• CAS: 7229-50-7
• 化学式: C₃₂H₄₄N₂O₉
• 分子量: 600.7
• InChiKey: KVTPRMVXYZKLIG-JWFPCVQRSA-N

物化性质

• 熔点：
  147-148°
• 比旋光度：
  D25 -93° (c = 1.6 in chloroform)
• 沸点：
  659.54°C (rough estimate)
• 密度：
  1.1852 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  9

制备方法与用途

生物活性

Streptolydigin (Portamycin) 是一种 3-乙酰基四酸抗生素，是一种有效的细菌 RNA 聚合酶 (bacterial RNA polymerase) 抑制剂，Ki 为 18 μM，Kd 为 15 μM。Streptolydigin 通过与 RNA 聚合酶结合来抑制 RNA 合成 (RNA synthesis)，但不抑制真核生物 RNA 聚合酶。Streptolydigin 具有强大的抗菌活性，特别是对厌氧菌和一些革兰氏阳性需氧菌。

靶点

Ki: 18 μM (Bacterial RNA polymerase)
Kd: 15 μM (Bacterial RNA polymerase)

体外研究

The antibiotic Streptolydigin (Stl) is a derivative of 3-acetyltetramic acid. Binding of Streptolydigin to RNA polymerase strictly depends on a noncatalytic magnesium ion which is likely chelated by the aspartate of the bridge helix of the active center.
Streptolydigin inhibits T. thermophilus RNA polymerase with a K _i of 1.8 μM.
Streptolydigin (Stl) inhibits initiation, elongation, and pyrophosphorolysis by bacterial RNA polymerase. Streptolydigin interacts with three structural elements within RNAP: the Stl pocket, the bridge helix, and the trigger-loop region. The Streptolydigin streptolol moiety interacts with the Streptolydigin pocket and bridge helix, and the Streptolydigin tetramic-acid moiety interacts with the trigger-loop region.