methyl (6S,9R,14S,17R,20R)-14-((R)-5-methoxy-5-oxo-4-(2,2,2-trifluoroacetamido)pentyl)-9-(methoxycarbonyl)-2,2,6,17,20-pentamethyl-4,7,12,15,18-pentaoxo-3-oxa-5,8,13,16,19-pentaazahenicosan-21-oate | 1426801-27-5

• 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: methyl (6S,9R,14S,17R,20R)-14-((R)-5-methoxy-5-oxo-4-(2,2,2-trifluoroacetamido)pentyl)-9-(methoxycarbonyl)-2,2,6,17,20-pentamethyl-4,7,12,15,18-pentaoxo-3-oxa-5,8,13,16,19-pentaazahenicosan-21-oate
• CAS: 1426801-27-5
• 化学式: C₃₁H₄₉F₃N₆O₁₃
• 分子量: 770.758
• InChiKey: PABFQRSFBXYKQN-WMDIELAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  53.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  262.73
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl (6S,9R,14S,17R,20R)-14-((R)-5-methoxy-5-oxo-4-(2,2,2-trifluoroacetamido)pentyl)-9-(methoxycarbonyl)-2,2,6,17,20-pentamethyl-4,7,12,15,18-pentaoxo-3-oxa-5,8,13,16,19-pentaazahenicosan-21-oate 在 盐酸 作用下， 以 水 为溶剂， 反应 0.33h， 生成 methyl (2R,5R,8S,13R,16S)-16-amino-8-((R)-5-methoxy-5-oxo-4-(2,2,2-trifluoroacetamido)pentyl)-13-(methoxycarbonyl)-2,5-dimethyl-4,7,10,15-tetraoxo-3,6,9,14-tetraazaheptadecanoate hydrochloride
  参考文献：
  名称：

  Forming Cross-Linked Peptidoglycan from Synthetic Gram-Negative Lipid II

  摘要：

  The bacterial cell wall precursor, Lipid II, has a highly conserved structure among different organisms except for differences in the amino acid sequence of the peptide side chain. Here, we report an efficient and flexible synthesis of the canonical Lipid II precursor required for the assembly of Gram-negative peptidoglycan (PG). We use a rapid LC/MS assay to analyze PG glycosyltransfer (PGT) and transpeptidase (TP) activities of Escherichia coli penicillin binding proteins PBP1A and PBP1B and show that the native m-DAP residue in the peptide side chain of Lipid II is required in order for TP-catalyzed peptide cross-linking to occur in vitro. Comparison of PG produced from synthetic canonical E. coli Lipid II with PG isolated from E. coli cells demonstrates that we can produce PG in vitro that resembles native structure. This work provides the tools necessary for reconstituting cell wall synthesis, an essential cellular process and major antibiotic target, in a purified system.

  DOI：

  10.1021/ja312510m
• 作为产物：
  描述：

  D-烯丙基甘氨酸 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 palladium on carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 35.83h， 生成 methyl (6S,9R,14S,17R,20R)-14-((R)-5-methoxy-5-oxo-4-(2,2,2-trifluoroacetamido)pentyl)-9-(methoxycarbonyl)-2,2,6,17,20-pentamethyl-4,7,12,15,18-pentaoxo-3-oxa-5,8,13,16,19-pentaazahenicosan-21-oate
  参考文献：
  名称：

  Forming Cross-Linked Peptidoglycan from Synthetic Gram-Negative Lipid II

  摘要：

  The bacterial cell wall precursor, Lipid II, has a highly conserved structure among different organisms except for differences in the amino acid sequence of the peptide side chain. Here, we report an efficient and flexible synthesis of the canonical Lipid II precursor required for the assembly of Gram-negative peptidoglycan (PG). We use a rapid LC/MS assay to analyze PG glycosyltransfer (PGT) and transpeptidase (TP) activities of Escherichia coli penicillin binding proteins PBP1A and PBP1B and show that the native m-DAP residue in the peptide side chain of Lipid II is required in order for TP-catalyzed peptide cross-linking to occur in vitro. Comparison of PG produced from synthetic canonical E. coli Lipid II with PG isolated from E. coli cells demonstrates that we can produce PG in vitro that resembles native structure. This work provides the tools necessary for reconstituting cell wall synthesis, an essential cellular process and major antibiotic target, in a purified system.

  DOI：

  10.1021/ja312510m