2-[(2S,5S,12S,15S,18S)-5-((S)-sec-Butyl)-18-(9H-fluoren-9-ylmethoxycarbonylamino)-15-hydroxymethyl-2-isopropyl-3,6,14,17,21-pentaoxo-1,4,7,13,16-pentaaza-cyclohenicos-12-yl]-thiazole-4-carboxylic acid ethyl ester | 882427-06-7

• 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-[(2S,5S,12S,15S,18S)-5-((S)-sec-Butyl)-18-(9H-fluoren-9-ylmethoxycarbonylamino)-15-hydroxymethyl-2-isopropyl-3,6,14,17,21-pentaoxo-1,4,7,13,16-pentaaza-cyclohenicos-12-yl]-thiazole-4-carboxylic acid ethyl ester
• CAS: 882427-06-7
• 化学式: C₄₅H₅₉N₇O₁₀S
• 分子量: 890.07
• InChiKey: FRWJIWWWGPCUPC-YGPHNRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  63.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  243.25
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-[(2S,5S,12S,15S,18S)-5-((S)-sec-Butyl)-18-(9H-fluoren-9-ylmethoxycarbonylamino)-15-hydroxymethyl-2-isopropyl-3,6,14,17,21-pentaoxo-1,4,7,13,16-pentaaza-cyclohenicos-12-yl]-thiazole-4-carboxylic acid ethyl ester 在 四甲基氢氧化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以93%的产率得到2-[(2S,5S,12S,15S,18S)-18-Amino-5-((S)-sec-butyl)-15-hydroxymethyl-2-isopropyl-3,6,14,17,21-pentaoxo-1,4,7,13,16-pentaaza-cyclohenicos-12-yl]-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Self-Condensation of a Thiazole-Peptide Bearing a 21-Membered Loop into a Library of Giant Macrocycles with Multiple Orthogonal Loops

  摘要：

  Tetrapeptide analogue H-[Glu-Ser-Lys(Thz)]-OH, containing a turn-inducing thiazole constraint, was used as a template to produce a 21-membered structurally characterized loop by linking Glu and Lys side chains with a Val-Ile dipeptide. This template was oligomerized in one pot to a library (cyclo-[1](n), n = 2-10) of giant symmetrical macrocycles (up to 120-membered rings), fused to 2-10 appended loops that were carried intact through multiple oligomerization (chain extension) and cyclization (chain terminating) reactions of the template. A three-dimensional solution structure for cyclo-[1](3) shows all three appended loops projecting from the same face of the macrocycle. This is a promising approach to separating pepticle motifs over large distances.

  DOI：

  10.1021/ol052842e
• 作为产物：
  描述：

  2-(5-[2-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-methyl-pentanoylamino]-1-{2-[4-tert-butoxycarbonyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-3-hydroxy-propionylamino}-pentyl)-thiazole-4-carboxylic acid ethyl ester 在 三异丙基硅烷 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 2-[(2S,5S,12S,15S,18S)-5-((S)-sec-Butyl)-18-(9H-fluoren-9-ylmethoxycarbonylamino)-15-hydroxymethyl-2-isopropyl-3,6,14,17,21-pentaoxo-1,4,7,13,16-pentaaza-cyclohenicos-12-yl]-thiazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Self-Condensation of a Thiazole-Peptide Bearing a 21-Membered Loop into a Library of Giant Macrocycles with Multiple Orthogonal Loops

  摘要：

  Tetrapeptide analogue H-[Glu-Ser-Lys(Thz)]-OH, containing a turn-inducing thiazole constraint, was used as a template to produce a 21-membered structurally characterized loop by linking Glu and Lys side chains with a Val-Ile dipeptide. This template was oligomerized in one pot to a library (cyclo-[1](n), n = 2-10) of giant symmetrical macrocycles (up to 120-membered rings), fused to 2-10 appended loops that were carried intact through multiple oligomerization (chain extension) and cyclization (chain terminating) reactions of the template. A three-dimensional solution structure for cyclo-[1](3) shows all three appended loops projecting from the same face of the macrocycle. This is a promising approach to separating pepticle motifs over large distances.

  DOI：

  10.1021/ol052842e