(2S)-3-hydroxy-2-({2-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]acetyl}amino)propanoic acid | 890901-69-6

• 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
• 英文名称: (2S)-3-hydroxy-2-({2-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]acetyl}amino)propanoic acid
• 英文别名: (2S)-3-hydroxy-2-[[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]propanoic acid
• CAS: 890901-69-6
• 化学式: C₁₀H₁₃N₃O₆
• 分子量: 271.23
• InChiKey: RLNORWDOXRCXSN-LURJTMIESA-N

物化性质

• 熔点：
  218-219 °C
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-3-hydroxy-2-({2-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]acetyl}amino)propanoic acid 、 4-甲氧基三苯基氯甲烷 在 吡啶 作用下， 反应 13.0h， 生成 4-O-monomethoxytrityl-N-(thymine-1-ylacetyl)-L-serine
  参考文献：
  名称：

  Synthesis of a novel ester analog of nucleic acids bearing a serine backbone

  摘要：

  A novel analog of nucleic acids bearing an optically active serine ester backbone, serine-based nucleobase-linked polyester (SNE), was synthesized. Monomers containing a thymine base were synthesized from L- and D-serines. Furthermore, reaction conditions were thoroughly examined for the ester bond formation by using a new phosphonium-type condensing reagent oil a solid support without racemization. The release of the dimer from the resin was also investigated using a new type of linker, which could be cleaved under neutral conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.076
• 作为产物：
  描述：

  1-thyminylacetic acid pentafluorophenyl ester 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2S)-3-hydroxy-2-({2-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]acetyl}amino)propanoic acid
  参考文献：
  名称：

  Synthesis of a novel ester analog of nucleic acids bearing a serine backbone

  摘要：

  A novel analog of nucleic acids bearing an optically active serine ester backbone, serine-based nucleobase-linked polyester (SNE), was synthesized. Monomers containing a thymine base were synthesized from L- and D-serines. Furthermore, reaction conditions were thoroughly examined for the ester bond formation by using a new phosphonium-type condensing reagent oil a solid support without racemization. The release of the dimer from the resin was also investigated using a new type of linker, which could be cleaved under neutral conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.076

文献信息

• Chiral peptide nucleic acid monomers (PNAM) with modified backbones
  作者：Alan Roy Katritzky、Tamari Narindoshvili

  DOI：10.1039/b806141f

  日期：——

  of optically pure PNAMs comprising l- or d-serine, l-lysine and l-arginine units linked to thymine or Cbz-cytosine are described. Simple workup and inexpensive reagents are employed and free amino acids are used as coupling components.

  描述了包含与胸腺嘧啶或Cbz-胞嘧啶连接的1-或d-丝氨酸，1-赖氨酸和1-精氨酸单元的光学纯PNAM的方便的高产率合成。使用简单的后处理和廉价的试剂，并且将游离氨基酸用作偶联组分。