γ/δ-cis-tylosin | 950171-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: γ/δ-cis-tylosin
• 英文别名: tylosin；2-[(4R,5S,6S,7R,9R,11E,13Z,15R,16R)-6-[(2R,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
• CAS: 950171-77-4
• 化学式: C₄₆H₇₇NO₁₇
• 分子量: 916.114
• InChiKey: WBPYTXDJUQJLPQ-XYKXDWRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  64
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  239
• 氢给体数：
  5
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  酒石酸泰乐菌素 以 水 为溶剂， 生成 γ/δ-cis-tylosin
  参考文献：
  名称：

  Environmental Photochemistry of Tylosin:  Efficient, Reversible Photoisomerization to a Less-Active Isomer, Followed by Photolysis

  摘要：

  The environmental photochemical kinetics of tylosin, a common veterinary macrolide antibiotic and growth promoter, were investigated under simulated sunlight. An efficient, reversible photoisomerization was characterized using kinetic, mass spectrometry, and proton nuclear magnetic resonance data. The photoisomerization was confirmed to occur by a rotation about the distal alkene of the ketodiene functionality. Concurrent forward (quantum yield = 0.39 +/- 0.09) and back (quantum yield = 0.32 +/- 0.08) reactions lead to a photochemical equilibrium near a tylosin/photoisomer ratio of 50:50, completed in less than 2 min under a spectrum equivalent to noontime, summer sunlight. The activity of the isomer for the inhibition of Escherichia coli DH5 alpha growth was observed to be less than that of tylosin. On a longer time scale than that of isomerization, the isomer mixture undergoes photolysis with a quantum yield of (1.4 +/- 0.3) x 10(-3). The observed quantum yields and UV-vis absorbance data allow for the prediction of the photochemical behavior of tylosin in most environmental systems. Indirect photosensitization was not a significant loss process in solutions of Suwannee River fulvic acid with concentrations from 1 to 20 mg L-1.

  DOI：

  10.1021/jf070101h