2-({2-[2-(2-{[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-3-phenyl-propionylamino)-3-phenyl-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-phenyl-propionic acid methyl ester | 617688-75-2

• 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: 2-({2-[2-(2-{[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-3-phenyl-propionylamino)-3-phenyl-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-phenyl-propionic acid methyl ester
• CAS: 617688-75-2
• 化学式: C₆₂H₆₆N₆O₉
• 分子量: 1039.24
• InChiKey: MJNHOBFKXXOWJL-ZOPNQXNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  77.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  192.55
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-({2-[2-(2-{[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-3-phenyl-propionylamino)-3-phenyl-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-phenyl-propionic acid methyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Novel antibiotics: C-2 symmetrical macrocycles inhibiting Holliday junction DNA binding by E. coli RuvC

  摘要：

  Holliday junctions (HJs) are formed as transient DNA intermediates during site-specific and homologous recombination. Both of these genetic exchange pathways are critical for normal DNA metabolism and repair. Trapping HJs leads to bacterial cell death by preventing proper segregation of the resulting interlinked chromosomes. Macrocyclic peptides designed to target this intermediate were synthesized with the goal of identifying compounds with specificity for this unique molecular target. We discovered ten macrocycles, both hexameric and octameric peptides, capable of trapping HJs in vitro. Those macrocycles containing tyrosine residues proved most effective. These data demonstrate that C-2 symmetrical macrocycles offer excellent synthetic targets for the development of novel antibiotic agents. Furthermore, the active compounds identified provide valuable tools for probing different pathways of recombinational exchange. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.028
• 作为产物：
  描述：

  (S)-2-{[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester 在 苯甲醚 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-({2-[2-(2-{[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl]-amino}-3-phenyl-propionylamino)-3-phenyl-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Novel antibiotics: C-2 symmetrical macrocycles inhibiting Holliday junction DNA binding by E. coli RuvC

  摘要：

  Holliday junctions (HJs) are formed as transient DNA intermediates during site-specific and homologous recombination. Both of these genetic exchange pathways are critical for normal DNA metabolism and repair. Trapping HJs leads to bacterial cell death by preventing proper segregation of the resulting interlinked chromosomes. Macrocyclic peptides designed to target this intermediate were synthesized with the goal of identifying compounds with specificity for this unique molecular target. We discovered ten macrocycles, both hexameric and octameric peptides, capable of trapping HJs in vitro. Those macrocycles containing tyrosine residues proved most effective. These data demonstrate that C-2 symmetrical macrocycles offer excellent synthetic targets for the development of novel antibiotic agents. Furthermore, the active compounds identified provide valuable tools for probing different pathways of recombinational exchange. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.028

文献信息

• Novel Antibiotics:  Macrocyclic Peptides Designed to Trap Holliday Junctions
  作者：Megan L. Bolla、Enrique V. Azevedo、Jason M. Smith、Rachel E. Taylor、Dev K. Ranjit、Anca M. Segall、Shelli R. McAlpine

  DOI：10.1021/ol020204f

  日期：2003.1.1

  Described are the syntheses of eight macrocyclic peptides designed to trap Holliday junctions in bacteria, thereby inhibiting bacterial growth. These macrocycles were designed from linear dimerized hexapeptides that bind to the C-2 symmetrical Holliday junction. They were synthesized from three monomers using a combinatorial-like strategy that permits elucidation of the monomer role in accumulation of Holliday junctions and antibiotic activity. These macrocycles are an important step in designing and synthesizing a new class of antibiotics.