2-(Fmoc-aminomethyl)-oxazole-4-carboxylic acid | 182120-91-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(Fmoc-aminomethyl)-oxazole-4-carboxylic acid
• 英文别名: Fmoc-Gly-Ser(Oxz)-OH；2-(9H-Fluorene-9-ylmethoxycarbonylaminomethyl)oxazole-4-carboxylic acid；2-[(9H-fluoren-9-ylmethoxycarbonylamino)methyl]-1,3-oxazole-4-carboxylic acid
• CAS: 182120-91-8
• 化学式: C₂₀H₁₆N₂O₅
• 分子量: 364.357
• InChiKey: ZCGYFLSCIKFVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-甘氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 Fmoc-L-异亮氨酸 、 N-Fmoc-N'-三苯甲基-L-组氨酸 、 2-(Fmoc-aminomethyl)-oxazole-4-carboxylic acid 在 N-甲基吗啉 、 wang resin 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[[2-[[2-(aminomethyl)-1,3-oxazole-4-carbonyl]amino]acetyl]amino]methyl]-1,3-oxazole-4-carbonyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-methylpentanoic acid
  参考文献：
  名称：

  Total Synthesis of Microcin B17 via a Fragment Condensation Approach

  摘要：

  The total synthesis of the 43 amino acid antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.

  DOI：

  10.1021/ol102916b
• 作为产物：
  描述：

  2-((叔丁氧基羰基氨基)甲基)噁唑-4-羧酸 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 16.75h， 生成 2-(Fmoc-aminomethyl)-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Total Synthesis of Microcin B17 via a Fragment Condensation Approach

  摘要：

  The total synthesis of the 43 amino acid antibacterial peptide Microcin B17 (MccB17) is described. The natural product was synthesized via a convergent approach from a heterocycle-derived peptide and peptide thioester fragments prepared via Fmoc-strategy solid phase peptide synthesis (SPPS). Final assembly was achieved in an efficient manner using two Ag(I)-assisted peptide ligation reactions to afford MccB17 in excellent overall yield.

  DOI：

  10.1021/ol102916b

文献信息

• Oxazole and thiazole combinatorial libraries
  申请人：M. Martin Lenore

  公开号：US20060161007A1

  公开（公告）日：2006-07-20

  This invention provides a novel method for synthesizing an ensemble of peptides that allows for the generation of an unlimited number of antibiotic compounds. More specifically, the method comprises utilizes synthetic heterocyclic amino acids containing thaizole and/or oxazole as building blocks in a solid phase combinatorial synthesis to yield natural and unnatural antibiotic compounds.

  这项发明提供了一种合成多肽集合的新方法，允许生成无限数量的抗生素化合物。更具体地，该方法利用含有噻唑和/或噁唑的合成杂环氨基酸作为固相组合合成的构建单元，以产生天然和非天然的抗生素化合物。
• OXAZOLE AND THIAZOLE COMBINATORIAL LIBRARIES
  申请人：Martin Lenore M.

  公开号：US20100113305A1

  公开（公告）日：2010-05-06

  This invention provides a novel method for synthesizing an ensemble of peptides that allows for the generation of an unlimited number of antibiotic compounds. More specifically, the method comprises utilizes synthetic heterocyclic amino acids containing thaizole and/or oxazole as building blocks in a solid phase combinatorial synthesis to yield natural and unnatural antibiotic compounds.

  这项发明提供了一种新颖的合成肽的方法，允许生成无限数量的抗生素化合物。更具体地，该方法利用含有噻唑和/或异噁唑的合成杂环氨基酸作为固相组合合成中的构建块，以产生天然和非天然的抗生素化合物。
• Videnov, Georgi; Kaiser, Dietmar; Kempter, Christoph, Angewandte Chemie, 1996, vol. 108, # 13/14, p. 1604 - 1607
  作者：Videnov, Georgi、Kaiser, Dietmar、Kempter, Christoph、Jung, Guenther

  DOI：——

  日期：——
• EP1169311A4
  申请人：——

  公开号：EP1169311A4

  公开（公告）日：2004-09-15
• [EN] OXAZOLE AND THIAZOLE COMBINATORIAL LIBRARIES<br/>[FR] BANQUES COMBINATOIRES D'OXAZOLE ET DE THIAZOLE
  申请人：RHODE ISLAND EDUCATION

  公开号：WO2000056724A1

  公开（公告）日：2000-09-28

  This invention provides a novel method for synthesizing an ensemble of peptides that allows for the generation of an unlimited number of antibiotic compounds. More specifically, the method comprises utilizes synthetic heterocyclic amino acides containing thaizole and/or oxazole as building blocks in a solid phase combinatorial synthesis to yield natural and unnatural antibiotic compounds.