tert-butyl(1-(3-(((3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)carbamoyl)-4,5-dihydroxyphenyl)-1-oxo-5,8,11-trioxa-2-azatridecan-13-yl)carbamate | 1407510-87-5

• 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: tert-butyl(1-(3-(((3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)carbamoyl)-4,5-dihydroxyphenyl)-1-oxo-5,8,11-trioxa-2-azatridecan-13-yl)carbamate
• CAS: 1407510-87-5
• 化学式: C₈₆H₈₉N₅O₂₁
• 分子量: 1528.67
• InChiKey: JGCXXKVQVKYFJU-ZVXTYOKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  112.0
• 可旋转键数：
  37.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  316.7
• 氢给体数：
  5.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  tert-butyl(1-(3-(((3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)carbamoyl)-4,5-dihydroxyphenyl)-1-oxo-5,8,11-trioxa-2-azatridecan-13-yl)carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以50%的产率得到tert-butyl(1-(3-(((3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)carbamoyl)-4,5-dihydroxyphenyl)-1-oxo-5,8,11-trioxa-2-azatridecan-13-yl)carbamate
  参考文献：
  名称：

  ENTEROBACTIN CONJUGATES AND USES THEREOF

  摘要：

  本发明提供了新型肠杆菌铁胞内载体共轭物，如式(I)化合物及其盐，其中X是载体，可以是抗生素、荧光素或生物素。本发明还提供了涉及式(I)化合物的络合物、组合物、试剂盒和方法，用于将载体传递给细菌，治疗受试者的细菌感染、囊性纤维化和/或炎症性肠病，预防受试者的细菌感染、囊性纤维化和/或炎症性肠病，抑制或杀死细菌的生长，或确定生物样品中细菌的浓度。在某些实施例中，细菌是革兰氏阴性细菌。

  公开号：

  US20150105337A1
• 作为产物：
  描述：

  3-[2-(2-(2-氨基乙氧基)乙氧基)乙氧基]丙酸叔丁酯 、 3,4-bis(benzyloxy)-5-(((3S,7S,11S)-7,11-bis(2,3-bis(benzyloxy)benzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)carbamoyl)benzoic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以75%的产率得到tert-butyl(1-(3-(((3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl)carbamoyl)-4,5-dihydroxyphenyl)-1-oxo-5,8,11-trioxa-2-azatridecan-13-yl)carbamate
  参考文献：
  名称：

  ENTEROBACTIN CONJUGATES AND USES THEREOF

  摘要：

  本发明提供了新型肠杆菌铁胞内载体共轭物，如式(I)化合物及其盐，其中X是载体，可以是抗生素、荧光素或生物素。本发明还提供了涉及式(I)化合物的络合物、组合物、试剂盒和方法，用于将载体传递给细菌，治疗受试者的细菌感染、囊性纤维化和/或炎症性肠病，预防受试者的细菌感染、囊性纤维化和/或炎症性肠病，抑制或杀死细菌的生长，或确定生物样品中细菌的浓度。在某些实施例中，细菌是革兰氏阴性细菌。

  公开号：

  US20150105337A1

文献信息

• Siderophore-Mediated Cargo Delivery to the Cytoplasm of <i>Escherichia coli</i> and <i>Pseudomonas aeruginosa</i>: Syntheses of Monofunctionalized Enterobactin Scaffolds and Evaluation of Enterobactin–Cargo Conjugate Uptake
  作者：Tengfei Zheng、Justin L. Bullock、Elizabeth M. Nolan

  DOI：10.1021/ja3077268

  日期：2012.11.7

  The design and syntheses of monofunctionalized enterobactin (Ent, L- and D-isomers) scaffolds where one catecholate moiety of enterobactin houses an alkene, aldehyde, or carboxylic acid at the C5 position are described. These molecules are key precursors to a family of 10 enterobactin-cargo conjugates presented in this work, which were designed to probe the extent to which the Gram-negative ferric enterobactin uptake and processing machinery recognizes, transports, and utilizes derivatized enterobactin scaffolds. A series of growth recovery assays employing enterobactin-deficient E. coli ATCC 33475 (ent-) revealed that six conjugates based on L-Ent having relatively small cargos promoted E. coli growth under iron limiting conditions whereas negligible-to-no growth recovery was observed for four conjugates with relatively large cargos. No growth recovery was observed for the enterobactin receptor deficient strain of E. coli H1187 (fepA-) or the enterobactin esterase deficient derivative of E. coli K-12 JW0576 (fes-), or when the D-isomer of enterobactin was employed These results demonstrate that the E. coli ferric enterobactin transport machinery identifies and delivers select cargo-modified scaffolds to the E. coli cytoplasm. Pseudomonas aeruginosa PAO1 K648 (pvd-, pch-) exhibited greater promiscuity than that of E. coli for the uptake and utilization of the enterobactin-cargo conjugates, and growth promotion was observed for eight conjugates under iron-limiting conditions. Enterobactin may be utilized for delivering molecular cargos via its transport machinery to the cytoplasm of E. coli and P. aeruginosa thereby providing a means to overcome the Gram-negative outer membrane permeability barrier.