(1S,2R,19R,22S,34S,37R,40R,52S)-22-amino-5,15-dichloro-2,26,31,44,47,49,64-heptahydroxy-21,35,38,54,56,59-hexaoxo-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid | 89139-42-4

• 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
• 英文名称: (1S,2R,19R,22S,34S,37R,40R,52S)-22-amino-5,15-dichloro-2,26,31,44,47,49,64-heptahydroxy-21,35,38,54,56,59-hexaoxo-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid
• CAS: 89139-42-4
• 化学式: C₅₈H₄₅Cl₂N₇O₁₈
• 分子量: 1198.94
• InChiKey: DKVBOUDTNWVDEP-YHXGLDAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  85
• 可旋转键数：
  1
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  407
• 氢给体数：
  15
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (1S,2R,19R,22S,34S,37R,40R,52S)-22-amino-5,15-dichloro-2,26,31,44,47,49,64-heptahydroxy-21,35,38,54,56,59-hexaoxo-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid 在 sodium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 水 、 乙腈 为溶剂， 生成 (1S,2R,19R,34S,37R,40R,52S)-5,15-dichloro-2,26,31,44,47,49,64-heptahydroxy-21,35,38,54,56,59-hexaoxo-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid
  参考文献：
  名称：

  Deaminoteicoplanin and its derivatives. Synthesis, antibacterial activity, and binding strength to Ac-D-Ala-D-Ala

  摘要：

  Teicoplanin and its acid hydrolysis products were deaminated with hydroxylamine-O-sulfonic acid (HOS). A few amides of these deaminoteicoplanins were also prepared. The loss of the terminal amino group reduces in vitro activity against staphylococcal and streptococcal bacteria to one-half to one-third, while binding strength to Ac-D-Ala-D-Ala, measured by differential UV spectroscopy, is reduced to one-tenth that of teicoplanin. The in vitro activity is further reduced by the presence of serum, and this is attributable to the increased lipophilicity and total negative charge of the deamino compounds. Comparison of UV spectra of deaminoteicoplanins with those of parent compounds made it possible to single out the most acid phenol group of teicoplanin aglycon (OH-4; pK = 8.2).

  DOI：

  10.1021/jm00122a007
• 作为产物：
  描述：

  在 o.1 M phosphate buffer, pH 7.0 作用下， 以 水 为溶剂， 生成 (2R)-2-[[(2R)-2-[[(2S)-6-乙酰氨基-2-[(5-二甲基氨基萘-1-基)磺酰基氨基]己酰]氨基]丙酰]氨基]丙酸 、 (1S,2R,19R,22S,34S,37R,40R,52S)-22-amino-5,15-dichloro-2,26,31,44,47,49,64-heptahydroxy-21,35,38,54,56,59-hexaoxo-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid
  参考文献：
  名称：

  模型三肽与替考拉宁和类似半合成抗生素结合的动力学和热力学。

  摘要：

  模型三肽ε-N-乙酰基-α-N-丹酰-L-Lys-D-Ala-D-Ala（ADLAA）或α-N，ε-N-二乙酰基-L-Lys-的结合的热力学和动力学替考拉宁（1a）的D-Ala-D-Ala（AALAA）和一系列具有（1b-f）或不含（2a-g）糖苷侧臂并在肽主链末端氨基酸修饰的半合成衍生物已经通过荧光或紫外光谱研究。建议绑定过程通过两步机制进行。第一个快速过程很可能分别受底物肽链和抗生素肽链的C和N末端之间的静电相互作用支配，而第二个较慢的过程则解释了氢键的形成对整体约束力的主要贡献。所有修饰衍生物的结合常数均小于天然替考拉宁的结合常数。当除去糖残基时，观察到总结合常数的较大变化，而当肽链的N端被酰化时，观察到较小程度的变化。动力学过程受引入的修饰影响很小。

  DOI：

  10.1021/jo9605556

文献信息

• Kinetics and Thermodynamics of Binding of a Model Tripeptide to Teicoplanin and Analogous Semisynthetic Antibiotics
  作者：Paolo Scrimin、Paolo Tecilla、Umberto Tonellato、Massimo Verzini、Bianca Patrizia Andreini、John E. Coutant、Luigi F. Zerilli

  DOI：10.1021/jo9605556

  日期：1996.1.1

  thermodynamics and kinetics of binding of model tripeptides epsilon-N-acetyl-alpha-N-dansyl-L-Lys-D-Ala-D-Ala (ADLAA) or alpha-N,epsilon-N-diacetyl-L-Lys-D-Ala-D-Ala (AALAA) to teicoplanin (1a) and a series of semisynthetic derivatives with (1b-f) or devoid of (2a-g) the glycidic side arms and modified at the terminal amino acids of the peptide backbone have been studied by fluorescence or UV spectroscopy. The binding

  模型三肽ε-N-乙酰基-α-N-丹酰-L-Lys-D-Ala-D-Ala（ADLAA）或α-N，ε-N-二乙酰基-L-Lys-的结合的热力学和动力学替考拉宁（1a）的D-Ala-D-Ala（AALAA）和一系列具有（1b-f）或不含（2a-g）糖苷侧臂并在肽主链末端氨基酸修饰的半合成衍生物已经通过荧光或紫外光谱研究。建议绑定过程通过两步机制进行。第一个快速过程很可能分别受底物肽链和抗生素肽链的C和N末端之间的静电相互作用支配，而第二个较慢的过程则解释了氢键的形成对整体约束力的主要贡献。所有修饰衍生物的结合常数均小于天然替考拉宁的结合常数。当除去糖残基时，观察到总结合常数的较大变化，而当肽链的N端被酰化时，观察到较小程度的变化。动力学过程受引入的修饰影响很小。
• Deaminoteicoplanin and its derivatives. Synthesis, antibacterial activity, and binding strength to Ac-D-Ala-D-Ala
  作者：Aldo Trani、Pietro Ferrari、Rosa Pallanza、Giorgio Tarzia

  DOI：10.1021/jm00122a007

  日期：1989.2

  Teicoplanin and its acid hydrolysis products were deaminated with hydroxylamine-O-sulfonic acid (HOS). A few amides of these deaminoteicoplanins were also prepared. The loss of the terminal amino group reduces in vitro activity against staphylococcal and streptococcal bacteria to one-half to one-third, while binding strength to Ac-D-Ala-D-Ala, measured by differential UV spectroscopy, is reduced to one-tenth that of teicoplanin. The in vitro activity is further reduced by the presence of serum, and this is attributable to the increased lipophilicity and total negative charge of the deamino compounds. Comparison of UV spectra of deaminoteicoplanins with those of parent compounds made it possible to single out the most acid phenol group of teicoplanin aglycon (OH-4; pK = 8.2).