Fmoc-Ser{PO[OH][OAMP(acetonide)]}-OH | 1380098-61-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: Fmoc-Ser{PO[OH][OAMP(acetonide)]}-OH
• 英文别名: (2S)-3-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-hydroxyphosphoryl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 1380098-61-2
• 化学式: C₃₁H₃₃N₆O₁₁P
• 分子量: 696.61
• InChiKey: KMXSAPIZNGVCDZ-AKIIDSJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  229
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-Ser{PO[OH][OAMP(acetonide)]}-OH 、 Fmoc-L-脯氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-O-叔丁基-L-谷氨酸 、 Fmoc-O-叔丁基-L-酪氨酸 、 Fmoc-O-叔丁基-L-苏氨酸 、 Fmoc-N-三苯甲基-L-天冬酰胺 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以17%的产率得到
  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：

  在 四(三苯基膦)钯 、 间氯过氧苯甲酸 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 Fmoc-Ser{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

文献信息

• Fmoc-based solid-phase synthesis of adenylylated peptides using diester-type adenylylated amino acid derivatives
  作者：Keiji Ogura、Akira Shigenaga、Koji Ebisuno、Hiroko Hirakawa、Akira Otaka

  DOI：10.1016/j.tetlet.2012.04.063

  日期：2012.7

  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.