(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
• Structural Modifications of the Active Site in Teicoplanin and Related Glycopeptides. 1. Reductive Hydrolysis of the 1,2- and 2,3-Peptide Bonds
  作者：Adriano Malabarba、Romeo Ciabatti、Jürgen Kettenring、Pietro Ferrari、Károly Vékey、Elvio Bellasio、Maurizio Denaro

  DOI：10.1021/jo941809v

  日期：1996.1.1

  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.
• Role of the Glycopeptide Framework in the Antibacterial Activity of Hydrophobic Derivatives of Glycopeptide Antibiotics
  作者：Svetlana S. Printsevskaya、Andrey Y. Pavlov、Evgenia N. Olsufyeva、Elena P. Mirchink、Maria N. Preobrazhenskaya

  DOI：10.1021/jm020320o

  日期：2003.3.1

  The antibacterial properties of glycopeptide antibiotics are based on their interaction with the d-Ala-d-Ala containing pentapeptide of bacterial peptidoglycan. The hydrophobic amides of vancomycin (1), teicoplanin (2), teicoplanin aglycon (3), and eremomycin (4) were compared with similar amides of minimally or low active des-(N-methyl-d-leucyl)eremomycin (5), eremomycin aglycon (6), des-(N-methy

  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）