(1S,2R,19R,22R,34S,37R,40R,52S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22,34-diamino-5,15-dichloro-26,31,44,49,62-pentahydroxy-19-(hydroxymethyl)-21,35,38,54,56-pentaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55-pentazadecacyclo[38.14.2.23,6.214,17.18,12.123,27.129,33.141,45.010,37.046,51]tetrahexaconta-3,5,8,10,12(62),14,16,23(59),24,26,29(58),30,32,41(57),42,44,46(51),47,49,60,63-henicosaene-52-carboxylic acid | 133823-78-6

• 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,22R,34S,37R,40R,52S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22,34-diamino-5,15-dichloro-26,31,44,49,62-pentahydroxy-19-(hydroxymethyl)-21,35,38,54,56-pentaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55-pentazadecacyclo[38.14.2.23,6.214,17.18,12.123,27.129,33.141,45.010,37.046,51]tetrahexaconta-3,5,8,10,12(62),14,16,23(59),24,26,29(58),30,32,41(57),42,44,46(51),47,49,60,63-henicosaene-52-carboxylic acid
• CAS: 133823-78-6
• 化学式: C₇₂H₇₂Cl₂N₈O₂₈
• 分子量: 1568.31
• InChiKey: JUINADBIXLXLHF-OBIJVJPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  110
• 可旋转键数：
  9
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  592
• 氢给体数：
  22
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  (1S,2R,19R,22R,34S,37R,40R,52S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22,34-diamino-5,15-dichloro-26,31,44,49,62-pentahydroxy-19-(hydroxymethyl)-21,35,38,54,56-pentaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55-pentazadecacyclo[38.14.2.23,6.214,17.18,12.123,27.129,33.141,45.010,37.046,51]tetrahexaconta-3,5,8,10,12(62),14,16,23(59),24,26,29(58),30,32,41(57),42,44,46(51),47,49,60,63-henicosaene-52-carboxylic acid 在 吡啶 、 硫代异氰酸苯酯 、 三乙胺 、 三氟乙酸 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 17.0h， 以30%的产率得到
  参考文献：
  名称：

  糖肽骨架在糖肽抗生素疏水衍生物的抗菌活性中的作用。

  摘要：

  糖肽类抗生素的抗菌特性是基于它们与细菌肽聚糖的五肽中含有d-Ala-d-Ala的相互作用。将万古霉素（1），替考拉宁（2），替考拉宁糖苷配基（3）和埃雷霉素（4）的疏水性酰胺与最低或低活性的des-（N-甲基-d-亮氨酰）埃雷霉素（5）的类似酰胺进行了比较，eremomycin苷元（6），des-（N-甲基-d-亮氨酰）eremomycin苷元（7）和替考拉宁降解产物TB-TPA（8）。1、3、4和6的所有疏水性酰胺对糖肽耐药性肠球菌（GRE）的活性几乎相同[最低抑制浓度（MIC）

  DOI：

  10.1021/jm020320o
• 作为产物：
  描述：

  teicoplanin A₃-1 在 sodium tetrahydroborate 、 水 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到(1S,2R,19R,22R,34S,37R,40R,52S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22,34-diamino-5,15-dichloro-26,31,44,49,62-pentahydroxy-19-(hydroxymethyl)-21,35,38,54,56-pentaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55-pentazadecacyclo[38.14.2.23,6.214,17.18,12.123,27.129,33.141,45.010,37.046,51]tetrahexaconta-3,5,8,10,12(62),14,16,23(59),24,26,29(58),30,32,41(57),42,44,46(51),47,49,60,63-henicosaene-52-carboxylic acid
  参考文献：
  名称：

  Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 1. Reductive Hydrolysis of the 1,2- and 2,3-Peptide Bonds

  摘要：

  Reaction of teicoplanin glycopeptides with sodium borohydride in aqueous ethanol solutions produced open pentapeptide derivatives in which the amide bond between amino acids 2 and 3 was hydrolyzed and the carboxyl group of amino acid 2 was reduced to a primary alcohol. Other glycopeptides of the dalbaheptide family, such as vancomycin, ristocetin, and A-40,926, underwent selective reductive hydrolysis (RH) of the heptapeptide backbone at the same position as in teicoplanins, while antibiotic A-42,867 and vancomycin hexapeptide were resistant. Also, teicoplanin and vancomycin were resistant to RH-treatment when the N-terminus was protected as carbamate. In contrast, open hexapeptides in which the 1,2-peptide bond was hydrolyzed and the carboxyl group of amino acid 1 was reduced to hydroxymethyl were obtained from carbamate derivatives of sugar-free compounds deglucoteicoplanin (TD) and vancomycin-aglycon (VA) under RH-conditions. Limited to BOC or CBZ-TD, the 3,4-amide bond was also affected. A possible RH-mechanism is proposed for natural glycopeptides and their derivatives. Teicoplanin-derived RH penta- and hexapeptides maintained residual antibacterial activity. As other analogous RH-glycopeptides, they are key intermediates for the synthesis of new members of this family of antibiotics. A synthetic approach to ring-closed derivatives of TD hexapeptide alcohol (TDHPA) and their activities are also reported.

  DOI：

  10.1021/jo941809v

文献信息

• Reductive Hydrolysis of the 59,60-Amide Bond of Teicoplanin Antibiotics: A Key Step from Natural to Synthetic Glycopeptides
  作者：Adriano Malabarba、Romeo Ciabatti

  DOI：10.1021/jm00045a002

  日期：1994.9