N-ethanoyl-5-(2,2,2-trifluoroethoxycarbonyl)-2'-deoxycytidine | 186601-15-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-ethanoyl-5-(2,2,2-trifluoroethoxycarbonyl)-2'-deoxycytidine
• 英文别名: N-acetyl-5-(2,2,2-trifluoroethoxycarbonyl)-2'-deoxycytidine；2,2,2-trifluoroethyl 4-acetamido-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidine-5-carboxylate
• CAS: 186601-15-0
• 化学式: C₁₄H₁₆F₃N₃O₇
• 分子量: 395.292
• InChiKey: KTFAZKSRFIDKHM-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-ethanoyl-5-(2,2,2-trifluoroethoxycarbonyl)-2'-deoxycytidine 在 吡啶 、 甲醇 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.17h， 生成 4-Amino-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid (6-acetylamino-hexyl)-amide
  参考文献：
  名称：

  Nucleosides and nucleotides. 161. Incorporation of 5-(N-aminoalkyl)carbamoyl-2′-deoxycytidines into oligodeoxyribonucleotides by a convenient post-synthetic modification method

  摘要：

  5-Trifluoroethoxycarbonyl-2'-deoxycytidine derivatives were synthesized and incorporated into oligonucleotides. The fully protected oligonucleotides were treated with diaminoethane or 1,6-diaminohexane to give oligonucleotides carrying amino-linkers, which were further derivatized with an intercalator. The properties of these oligonucleotides are described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00519-7
• 作为产物：
  描述：

  5-碘-2'-脱氧胞苷 在 二(氰基苯)二氯化钯 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-ethanoyl-5-(2,2,2-trifluoroethoxycarbonyl)-2'-deoxycytidine
  参考文献：
  名称：

  Nucleosides and nucleotides. 161. Incorporation of 5-(N-aminoalkyl)carbamoyl-2′-deoxycytidines into oligodeoxyribonucleotides by a convenient post-synthetic modification method

  摘要：

  5-Trifluoroethoxycarbonyl-2'-deoxycytidine derivatives were synthesized and incorporated into oligonucleotides. The fully protected oligonucleotides were treated with diaminoethane or 1,6-diaminohexane to give oligonucleotides carrying amino-linkers, which were further derivatized with an intercalator. The properties of these oligonucleotides are described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00519-7

文献信息

• [EN] CYTIDINE-5-CARBOXAMIDE MODIFIED NUCLEOTIDE COMPOSITIONS AND METHODS RELATED THERETO<br/>[FR] COMPOSITIONS NUCLÉOTIDIQUES DE CYTIDINES À MODIFICATION 5-CARBOXAMIDE ET PROCÉDÉS ASSOCIÉS
  申请人：SOMALOGIC INC

  公开号：WO2015077292A1

  公开（公告）日：2015-05-28

  Described herein are 5-position modified cytosine nucleotides and nucleosides as well as phosphoramidites and triphosphates derivatives thereof. Further provided are methods of making and using the same, and compositions and uses of the modified nucleosides as part of a nucleic acid molecule (e.g., aptamer).

  本文描述了5位修饰的胞嘧啶核苷酸和核苷以及它们的磷酰胺酰胺和三磷酸盐衍生物。此外还提供了制备和使用这些物质的方法，以及修饰核苷酸作为核酸分子（例如aptamer）一部分的组成和用途。
• Synthesis and properties of oligodeoxynucleotides containing 5-carboxy-2′-deoxycytidines
  作者：Masanori Sumino、Akihiro Ohkubo、Haruhiko Taguchi、Kohji Seio、Mitsuo Sekine

  DOI：10.1016/j.bmcl.2007.10.081

  日期：2008.1

  5-Carboxy-2'-deoxycytidine (dC(COO-)) was synthesized as an anion-carrier to seek a new possibility of modified oligodeoxynucleotides capable of stabilization of duplexes and triplexes. The base pairing properties of this compound were evaluated by use of ab initio calculations. These calculations suggest that the Hoogsteen-type base pair of dC(COO-)-G is less stable than that of the canonical C+-G

  合成5-羧基-2'-脱氧胞苷（dC（COO-））作为阴离子载体，以寻求能够稳定双链体和三链体的修饰寡脱氧核苷酸的新可能性。该化合物的碱基配对性质通过从头算计算来评估。这些计算表明，dC（COO-）-G的Hoogsteen型碱基对不如标准C + -G对的稳定，而dC（COO-）-G的Watson-Crick型碱基对则稍微稳定些。比天然GC碱基对稳定。修饰的胞嘧啶碱基显示出与胞嘧啶（pKa 4.2）相似的碱性。结果表明，掺入dC（COO-）的寡聚脱氧核苷酸13mer和14mer可以与互补的DNA寡聚体形成双链体，其比未修饰的双链体更稳定。相比之下，
• Cytidine-5-carboxamide modified nucleotide compositions and methods related thereto
  申请人：SomaLogic, Inc.

  公开号：US10239908B2

  公开（公告）日：2019-03-26

  Described herein are 5-position modified cytosine nucleotides and nucleosides as well as phosphoramidites and triphosphates derivatives thereof. Further provided are methods of making and using the same, and compositions and uses of the modified nucleosides as part of a nucleic acid molecule (e.g., aptamer).

  本文描述的是 5 位修饰胞嘧啶核苷酸和核苷及其磷酰胺和三磷酸盐衍生物。此外，还提供了制造和使用这些核苷酸的方法，以及作为核酸分子（如适配体）一部分的修饰核苷酸的组合物和用途。
• CYTIDINE-5-CARBOXAMIDE MODIFIED NUCLEOTIDE COMPOSITIONS AND METHODS RELATED THERETO
  申请人：Somalogic, Inc.

  公开号：EP3071588A1

  公开（公告）日：2016-09-28
• Cytidine-5-Carboxamide Modified Nucleotide Compositions and Methods Related Thereto
  申请人：SOMALOGIC, INC.

  公开号：US20160215013A1

  公开（公告）日：2016-07-28

  Described herein are 5-position modified cytosine nucleotides and nucleosides as well as phosphoramidites and triphosphates derivatives thereof. Further provided are methods of making and using the same, and compositions and uses of the modified nucleosides as part of a nucleic acid molecule (e.g., aptamer).