Fmoc-L-亮氨酰-亮氨酸 | 88743-98-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 亮氨酸类衍生物
• 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
• 中文名称: Fmoc-L-亮氨酰-亮氨酸
• 英文名称: (Fmoc)-Leu-Leu-OH
• 英文别名: Fmoc-Leu-Leu-OH；(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoyl]amino]-4-methylpentanoic acid
• CAS: 88743-98-0
• 化学式: C₂₇H₃₄N₂O₅
• 分子量: 466.577
• InChiKey: OLBBXRXTYWLDPL-ZEQRLZLVSA-N

物化性质

• 沸点：
  695.5±45.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-L-亮氨酰-亮氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  "Glycylcyclines". 3. 9-Aminodoxycyclinecarboxamides

  摘要：

  A series of 9-(acylamino)doxycycline derivatives has been prepared. These analogs exhibit good activity against both tetracycline sensitive and tetracycline resistant Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria that are encoded with the efflux and ribosomal resistance gene factors. N,N-Dialkylglycylamido derivatives possessed the highest activity. Replacement of glycine moiety with other amino acids did not further enhance the activity.

  DOI：

  10.1021/jm00046a003
• 作为产物：
  描述：

  Fmoc-Leu-Leu-OBzl 在 palladium 10% on activated carbon 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到Fmoc-L-亮氨酰-亮氨酸
  参考文献：
  名称：

  Glycopeptide probes for understanding peptide specificity of the folding sensor enzyme UGGT

  摘要：

  A systematic series of chitobiose-modified pentapeptides with sequence variations of hydrophobic leucine and hydrophilic serine were synthesized. The resulting glycopeptides were used as molecular probes to elucidate aglycon peptide specificity of the glycoprotein-folding sensor enzyme UGGT. Inhibitory experiments with a synthetic fluorescent glyco-substrate and the glycopeptides revealed that UGGT prefers a serine residue directly linked to C-terminal of the N-glycosylation site in its substrate recognition. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.013

文献信息

• Enzymatic synthesis of peptides on a solid support
  作者：Rose Haddoub、Martin Dauner、Fiona A. Stefanowicz、Valeria Barattini、Nicolas Laurent、Sabine L. Flitsch

  DOI：10.1039/b816847d

  日期：——

  PEGA resin (a copolymer of polyethylene glycol and polyacrylamide). Here we explore the scope of this methodology for using protected and glycosylated amino acids as well as the synthesis of longer peptides on resin and show that such a method can also be applied on non-porous surfaces, in particular on gold.

  先前我们已经表明，如果氨基组分固定在多孔PEGA树脂（聚乙二醇和聚丙烯酰胺的共聚物）上，则可以在水介质中使用蛋白酶催化从氨基酸高收率合成二肽。在这里，我们探索了使用受保护和糖基化氨基酸以及在树脂上合成更长的肽的这种方法的范围，并表明这种方法也可以应用于无孔表面，特别是金。
• Parallel Synthesis of Glycomimetic Libraries:  Targeting a C-Type Lectin
  作者：Michael C. Schuster、David A. Mann、Tonia J. Buchholz、Kathryn M. Johnson、William D. Thomas、Laura L. Kiessling

  DOI：10.1021/ol0340383

  日期：2003.5.1

  graphicWe have developed methods for the parallel synthesis of two libraries of non-carbohydrate-based analogues of mannose on a solid support. The natural product shikimic acid-was used as a key building block. The ability of the compounds to block the binding of the C-type lectin MBP-A to a mannosylated surface was assessed in a high-throughput assay. Ten library members with inhibitory activities equivalent to that of alpha-methyl mannopyranoside were identified.
• Solid-Phase Synthesis of Peptide Isosters by Nucleophilic Reactions with N-Terminal Peptide Aldehydes on a Polar Support Tailored for Solid-Phase Organic Chemistry
  作者：Jörg Rademann、Morten Meldal、Klaus Bock

  DOI：10.1002/(sici)1521-3765(19990401)5:4<1218::aid-chem1218>3.3.co;2-o

  日期：1999.4.1
• "Glycylcyclines". 3. 9-Aminodoxycyclinecarboxamides
  作者：Timothy C. Barden、Brian L. Buckwalter、Raymond T. Testa、Peter J. Petersen、Ving J. Lee

  DOI：10.1021/jm00046a003

  日期：1994.9

  A series of 9-(acylamino)doxycycline derivatives has been prepared. These analogs exhibit good activity against both tetracycline sensitive and tetracycline resistant Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria that are encoded with the efflux and ribosomal resistance gene factors. N,N-Dialkylglycylamido derivatives possessed the highest activity. Replacement of glycine moiety with other amino acids did not further enhance the activity.
• Glycopeptide probes for understanding peptide specificity of the folding sensor enzyme UGGT
  作者：Takaya Kudo、Makoto Hirano、Toshihiro Ishihara、Shun Shimura、Kiichiro Totani

  DOI：10.1016/j.bmcl.2014.11.013

  日期：2014.12

  A systematic series of chitobiose-modified pentapeptides with sequence variations of hydrophobic leucine and hydrophilic serine were synthesized. The resulting glycopeptides were used as molecular probes to elucidate aglycon peptide specificity of the glycoprotein-folding sensor enzyme UGGT. Inhibitory experiments with a synthetic fluorescent glyco-substrate and the glycopeptides revealed that UGGT prefers a serine residue directly linked to C-terminal of the N-glycosylation site in its substrate recognition. (C) 2014 Elsevier Ltd. All rights reserved.