Fmoc-Glu(OH)-1-OAll

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Fmoc-Glu(OH)-1-OAll
• 英文别名: methyl (2R)-2-(3-oxo-3-phenylsulfanylpropanoyl)oxy-3-trityloxypropanoate
• 化学式: C₂₃H₂₃N₂O₅Pol
• 分子量: 540.6
• InChiKey: FCDNOSNWEGPPHX-MUUNZHRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-Glu(OH)-1-OAll 在 四丁基氟化铵 、 silver trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 111.0h， 生成 (R)-5-hydroxymethyl-3-n-butoxycarbonyltetronic acid
  参考文献：
  名称：

  Efficient Synthesis of Dissymmetric Malonic Acid S,O-Esters via Monoalcoholysis of Symmetric Dithiomalonates under Neutral Conditions

  摘要：

  A novel method for the highly selective synthesis of dissymmetric S,O-malonates starting from symmetric diphenyl dithiomalonates under neutral conditions is described. The key step is the thermal formation of an acylketene, the stability of which would contribute to the selectivity. The synthetic utility of the dissymmetric S,O-malonates is also shown.

  DOI：

  10.1021/ol201744u
• 作为产物：
  描述：

  三苯基氯甲烷 在 4-二甲氨基吡啶 、 C₈H₆O₄^(2-)*Cu⁽²⁺⁾ 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 29.0h， 生成 Fmoc-Glu(OH)-1-OAll
  参考文献：
  名称：

  Efficient Synthesis of Dissymmetric Malonic Acid S,O-Esters via Monoalcoholysis of Symmetric Dithiomalonates under Neutral Conditions

  摘要：

  A novel method for the highly selective synthesis of dissymmetric S,O-malonates starting from symmetric diphenyl dithiomalonates under neutral conditions is described. The key step is the thermal formation of an acylketene, the stability of which would contribute to the selectivity. The synthetic utility of the dissymmetric S,O-malonates is also shown.

  DOI：

  10.1021/ol201744u

文献信息

• An Original Strategy for Gln Containing Peptide Synthesis Using SPPS and Glu(OH)-1-OAll
  作者：Ivaylo N. Minchev、Dantcho L. Danalev、Lyubomir T. Vezenkov、Lyubomira Nikolaeva-Glomb、Angel S. Galabov

  DOI：10.1007/s10989-010-9213-0

  日期：2010.12

  Using multiple peptide synthesis in parallel, a series of 24 compounds analogues of tripeptide sequence Z-Leu-Phe-Gln-H, modified by imidazole moiety were synthesized. An effective and simple scheme for including imidazole heterocycle to C- and/or N-terminus of Gln residue was created by means of allyl group as α-COOH protecting group for Fmoc-Glu. The approach using Fmoc-Glu-1-OAll as a first amino

  并行使用多个肽合成，合成了由咪唑部分修饰的一系列24个三肽序列Z-Leu-Phe-Gln-H的化合物类似物。通过烯丙基作为Fmoc-Glu的α-COOH保护基，创建了一个有效，简单的方案，将咪唑杂环包括到Gln残基的C和/或N端。使用Fmoc-Glu-1-OAll作为与树脂连接的第一个氨基酸的方法可用于合成大量氨基酸和/或包括化合物的杂环部分。根据初步的生物学试验，我们可以得出结论，咪唑杂环的存在对Coxsackieviruses B1和脊髓灰质炎病毒1型的抗病毒活性产生积极影响。
• Synthesis of the Bacteriocin Glycopeptide Sublancin 168 and <i>S</i>-Glycosylated Variants
  作者：Yves S. Y. Hsieh、Brendan L. Wilkinson、Mitchell R. O’Connell、Joel P. Mackay、Jacqueline M. Matthews、Richard J. Payne

  DOI：10.1021/ol300557g

  日期：2012.4.6

  The synthesis of sublancin 168, a unique S-glucosylated bacteriocin antibiotic, is described. The natural product and two S-glycosylated variants were successfully prepared via native chemical ligation followed by folding. The synthetic glycopeptides were shown to possess primarily an α-helical secondary structure by CD and NMR studies.

  描述了一种独特的S-葡萄糖基化细菌素抗生素sublancin 168的合成。通过天然化学连接然后折叠成功制备了天然产物和两个S-糖基化的变体。通过CD和NMR研究显示合成的糖肽主要具有α-螺旋二级结构。
• Efficient Synthesis of Dissymmetric Malonic Acid <i>S</i>,<i>O</i>-Esters via Monoalcoholysis of Symmetric Dithiomalonates under Neutral Conditions
  作者：Kazumasa Matsuo、Mitsuru Shindo

  DOI：10.1021/ol201744u

  日期：2011.8.19

  A novel method for the highly selective synthesis of dissymmetric S,O-malonates starting from symmetric diphenyl dithiomalonates under neutral conditions is described. The key step is the thermal formation of an acylketene, the stability of which would contribute to the selectivity. The synthetic utility of the dissymmetric S,O-malonates is also shown.