Fmoc-(R,R)-amino Boc-proline | 267230-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-(R,R)-amino Boc-proline
• 英文别名: Fmoc-AP(Boc)；Fmoc-(R,R)-AP(Boc)；(2R,3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
• CAS: 267230-39-7
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: JFLIEUQNMSCCTP-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2r)-Fmoc-2-氨基环戊烷羧酸 、 Fmoc-(R,R)-amino Boc-proline 生成
  参考文献：
  名称：

  Mimicry of Host-Defense Peptides by Unnatural Oligomers:  Antimicrobial β-Peptides

  摘要：

  We have designed beta-amino acid oligomers that are helical, cationic, and amphiphilic with the intention of mimicking the biological activity of amphiphilic, cationic a-helical antimicrobial peptides found in nature (e.g., magainins). We have previously identified a 17-residue beta-peptide (called beta-17) with antibiotic activity similar to that of a magainin derivative against four bacterial species, including two clinical isolates that are resistant to common antibiotics. This beta-peptide displays very low hemolytic activity against human red blood cells, which indicates selectivity for bacterial cells over mammalian cells. Here we examine some of the factors important for activity in this class of beta-peptides. An amphiphilic helix is necessary, because a nonamphiphilic isomer proved to be inactive. The ratio of cationic to hydrophobic residues is also important. Active beta-peptides induce the leakage of beta-galactosidase from treated Bacillus subtilis cells, as do a-helical antibiotic peptides, and this similarity suggests that the beta-peptide mode of action involves disruption of microbial membranes. This class of beta-peptides is not degraded by proteases, which bodes well for biological applications.

  DOI：

  10.1021/ja0260871
• 作为产物：
  描述：

  1-tert-butyl 2-ethyl (2R,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate 在 palladium on activated charcoal lithium hydroxide 、 三(2-氯乙基)胺 、 氢气 、 双氧水 、 碳酸氢钠 、 三苯基膦 、 tin(ll) chloride 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 水 、 丙酮 、 苯 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 反应 117.5h， 生成 Fmoc-(R,R)-amino Boc-proline
  参考文献：
  名称：

  Synthesis and 12-Helical Secondary Structure of β-Peptides Containing (2R,3R)-Aminoproline

  摘要：

  (2R,3R)-Aminoproline（一种基于吡咯啶的β-氨基酸）被合成并整合到六β-肽4中。该残基在环氮质子化时赋予水溶性，并允许在水溶液中形成12股螺旋结构。圆二色光谱显示了12股螺旋的特征，而12股螺旋结构通过二维核磁共振分析得到了确认。

  DOI：

  10.1021/ol0266370

文献信息

• Use of Parallel Synthesis To Probe Structure−Activity Relationships among 12-Helical β-Peptides:  Evidence of a Limit on Antimicrobial Activity
  作者：Emilie A. Porter、Bernard Weisblum、Samuel H. Gellman

  DOI：10.1021/ja0519785

  日期：2005.8.1

  We report structure-activity trends among helix-forming beta-amino acid oligomers that are intended to mimic alpha-helical host-defense peptides. Parallel synthesis of two small, focused beta-peptide libraries allowed us to identify relatively short (11-residue) beta-peptides that display antimicrobial activity. These beta-peptides exhibit selectivity for bacteria relative to human red blood cells. A large hydrophobic helical surface is necessary for antimicrobial activity. Longer analogues (16 residues) of the most active library members were prepared and evaluated. Some of these longer beta-peptides showed very good antimicrobial activity, but none was more active than a previously reported beta-peptide [Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H. Nature 2000, 404, 565]. The extensive literature on a-helical host-defense peptides and related alpha-peptides indicates that such molecules are seldom active at concentrations below 1 mu g/mL, and our results suggest that amphiphilic helical beta-peptides are subject to a comparable limit.
• Mimicry of Host-Defense Peptides by Unnatural Oligomers:  Antimicrobial β-Peptides
  作者：Emilie A. Porter、Bernard Weisblum、Samuel H. Gellman

  DOI：10.1021/ja0260871

  日期：2002.6.1

  We have designed beta-amino acid oligomers that are helical, cationic, and amphiphilic with the intention of mimicking the biological activity of amphiphilic, cationic a-helical antimicrobial peptides found in nature (e.g., magainins). We have previously identified a 17-residue beta-peptide (called beta-17) with antibiotic activity similar to that of a magainin derivative against four bacterial species, including two clinical isolates that are resistant to common antibiotics. This beta-peptide displays very low hemolytic activity against human red blood cells, which indicates selectivity for bacterial cells over mammalian cells. Here we examine some of the factors important for activity in this class of beta-peptides. An amphiphilic helix is necessary, because a nonamphiphilic isomer proved to be inactive. The ratio of cationic to hydrophobic residues is also important. Active beta-peptides induce the leakage of beta-galactosidase from treated Bacillus subtilis cells, as do a-helical antibiotic peptides, and this similarity suggests that the beta-peptide mode of action involves disruption of microbial membranes. This class of beta-peptides is not degraded by proteases, which bodes well for biological applications.
• Synthesis and 12-Helical Secondary Structure of β-Peptides Containing (2<i>R</i>,3<i>R</i>)-Aminoproline
  作者：Emilie A. Porter、Xifang Wang、Margaret A. Schmitt、Samuel H. Gellman

  DOI：10.1021/ol0266370

  日期：2002.9.1

  (2R,3R)-Aminoproline, A pyrrolidine-based beta-amino acid, was synthesized and incorporated into hexa-beta-peptide 4. This residue confers water solubility when the ring nitrogen is protonated and allows for 12-helix formation in aqueous solution. Circular dichroism spectra display the 12-helical signature, and 12-helical structure was confirmed by 2D NMR analysis.

  (2R,3R)-Aminoproline（一种基于吡咯啶的β-氨基酸）被合成并整合到六β-肽4中。该残基在环氮质子化时赋予水溶性，并允许在水溶液中形成12股螺旋结构。圆二色光谱显示了12股螺旋的特征，而12股螺旋结构通过二维核磁共振分析得到了确认。