Fmoc-Tyr{PO[OAllyl][OAMP(acetonide)]}-OAllyl | 1380098-66-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Fmoc-Tyr{PO[OAllyl][OAMP(acetonide)]}-OAllyl
• CAS: 1380098-66-7
• 化学式: C₄₃H₄₅N₆O₁₁P
• 分子量: 852.838
• InChiKey: OMRRVWUCFYRDAW-CMPDRPRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  61.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  206.7
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Tyr{PO[OAllyl][OAMP(acetonide)]}-OAllyl 在 四(三苯基膦)钯 、 N-甲基苯胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以46%的产率得到Fmoc-Tyr{PO[OH][OAMP(acetonide)]}-OH
  参考文献：
  名称：

  Fmoc-based solid-phase synthesis of adenylylated peptides using diester-type adenylylated amino acid derivatives

  摘要：

  Phosphodiester-type adenylylated (AMPylated) Ser, Thr, and Tyr derivatives were developed for Fmoc solid phase peptide synthesis of AMPylated peptides. One-pot/sequential reaction consisting of condensation of an N-nonprotected adenosine derivative and Fmoc-Ser/Thr/Tyr-OAllyl using allyl-N,N-diisopropylchlorophosphoramidite and subsequent oxidation with m-chloroperbenzoic acid gave phosphotriester-type AMPylated Ser/Thr/Tyr derivatives. After Pd(0)-mediated deprotection of allyl groups, the resulting phosphodiester-type AMPylated Ser/Thr/Tyr derivatives were successfully incorporated into peptides by standard Fmoc solid phase peptide synthesis without significant side reactions including dehydroalanine formation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.063
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 四氮唑 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 Fmoc-Tyr{PO[OAllyl][OAMP(acetonide)]}-OAllyl
  参考文献：
  名称：

  Fmoc-based solid-phase synthesis of adenylylated peptides using diester-type adenylylated amino acid derivatives

  摘要：

  Phosphodiester-type adenylylated (AMPylated) Ser, Thr, and Tyr derivatives were developed for Fmoc solid phase peptide synthesis of AMPylated peptides. One-pot/sequential reaction consisting of condensation of an N-nonprotected adenosine derivative and Fmoc-Ser/Thr/Tyr-OAllyl using allyl-N,N-diisopropylchlorophosphoramidite and subsequent oxidation with m-chloroperbenzoic acid gave phosphotriester-type AMPylated Ser/Thr/Tyr derivatives. After Pd(0)-mediated deprotection of allyl groups, the resulting phosphodiester-type AMPylated Ser/Thr/Tyr derivatives were successfully incorporated into peptides by standard Fmoc solid phase peptide synthesis without significant side reactions including dehydroalanine formation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.04.063