5-carboxylmethyl-2'-deoxycytidine | 1311141-22-6

• 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: 5-carboxylmethyl-2'-deoxycytidine
• 英文别名: 5-methoxycarbonyl-2'-deoxycytidine；methyl 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidine-5-carboxylate
• CAS: 1311141-22-6
• 化学式: C₁₁H₁₅N₃O₆
• 分子量: 285.257
• InChiKey: VBANHWHZJMYCHJ-XLPZGREQSA-N

物化性质

• 熔点：
  160-170 °C
• 沸点：
  538.3±60.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-carboxylmethyl-2'-deoxycytidine 在 水 、 lithium hydroxide 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以44%的产率得到5-carboxyl-2′-deoxycytidine
  参考文献：
  名称：

  Synthesis of 5-Hydroxymethyl-, 5-Formyl-, and 5-Carboxycytidine-triphosphates and Their Incorporation into Oligonucleotides by Polymerase Chain Reaction

  摘要：

  The synthesis of the triphosphates of 5-hydroxymethyl-, 5-formyl-, and 5-carboxycytidine and the incorporation of these building blocks into long DNA fragments using the polymerase chain reaction (PCR) are reported. In this way DNA fragments containing multiple hmC, fC, and caC nucleobases are readily accessible.

  DOI：

  10.1021/ol3033219
• 作为产物：
  描述：

  5-carboxylmethyl-3',5'-(tert-butyldimethylsilyl)-2'-deoxycytidine 在 吡啶 、 氟化氢吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 19.0h， 以73%的产率得到5-carboxylmethyl-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of 5-Hydroxymethyl-, 5-Formyl-, and 5-Carboxycytidine-triphosphates and Their Incorporation into Oligonucleotides by Polymerase Chain Reaction

  摘要：

  The synthesis of the triphosphates of 5-hydroxymethyl-, 5-formyl-, and 5-carboxycytidine and the incorporation of these building blocks into long DNA fragments using the polymerase chain reaction (PCR) are reported. In this way DNA fragments containing multiple hmC, fC, and caC nucleobases are readily accessible.

  DOI：

  10.1021/ol3033219

文献信息

• Catalytic Space Engineering as a Strategy to Activate C–H Oxidation on 5-Methylcytosine in Mammalian Genome
  作者：Sushma Sappa、Debasis Dey、Babu Sudhamalla、Kabirul Islam

  DOI：10.1021/jacs.1c03815

  日期：2021.8.11
• Syntheses of 5-Formyl- and 5-Carboxyl-dC Containing DNA Oligos as Potential Oxidation Products of 5-Hydroxymethylcytosine in DNA
  作者：Qing Dai、Chuan He

  DOI：10.1021/ol201189n

  日期：2011.7.1

  To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH4 produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.
• Synthesis of 5-Hydroxymethyl-, 5-Formyl-, and 5-Carboxycytidine-triphosphates and Their Incorporation into Oligonucleotides by Polymerase Chain Reaction
  作者：Barbara Steigenberger、Stefan Schiesser、Benjamin Hackner、Caterina Brandmayr、Silvia K. Laube、Jessica Steinbacher、Toni Pfaffeneder、Thomas Carell

  DOI：10.1021/ol3033219

  日期：2013.1.18

  The synthesis of the triphosphates of 5-hydroxymethyl-, 5-formyl-, and 5-carboxycytidine and the incorporation of these building blocks into long DNA fragments using the polymerase chain reaction (PCR) are reported. In this way DNA fragments containing multiple hmC, fC, and caC nucleobases are readily accessible.