2'-deoxy-2'-α-C-(amidomethyl)uridine | 171503-82-5

• 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: 2'-deoxy-2'-α-C-(amidomethyl)uridine
• 英文别名: 2-[(2R,3R,4S,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]acetamide
• CAS: 171503-82-5
• 化学式: C₁₁H₁₅N₃O₆
• 分子量: 285.257
• InChiKey: YEYIFKJUBLIRPX-FNIZFGCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 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：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-α-C-(amidomethyl)uridine 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-carbamoylmethyl-5-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  含2'- C-酰氨基烷基和2'- C-氰基烷基的寡脱氧核糖核苷酸的合成及其对互补DNA和RNA的杂交亲和力评估

  摘要：

  合成了含有2'- C-支链核苷且酰胺或腈附接到一个或两个碳烷基链上的寡脱氧核苷酸。制备2'- C-修饰的核苷的亚磷酰胺，并使用自动DNA合成将其掺入寡核苷酸中。通过紫外熔解实验测量了具有互补RNA和DNA的双链体稳定性，以评估酰胺/腈功能是否可以在不存在2'-氧的情况下诱导任何双链体稳定性。在没有2'-氧的情况下，含有2'- C-修饰的寡核苷酸的双链体稳定性降低。

  DOI：

  10.1016/j.tet.2006.11.024
• 作为产物：
  描述：

  2'-deoxy-2'-α-C-carboxymethyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 ammonium hydroxide 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.17h， 生成 2'-deoxy-2'-α-C-(amidomethyl)uridine
  参考文献：
  名称：

  Lawrence, Anthony J.; Pavey, John B. J.; Chan, Mai-Yee, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2761 - 2767

  摘要：

  DOI：

文献信息

• Sunthesis of functionalised 2′-C-branched nucleosides via their γ-butyrolactones
  作者：Anthony J. Lawrence、John B.J. Pavey、Ian A. O'Neil、Richard Cosstick

  DOI：10.1016/0040-4039(95)01226-8

  日期：1995.8

  Functionalised 2′-C-branched nucleosides that contain either a carboxylic acid (2), a primary amide (3) or a primary hydroxyl (4) group have been prepared and their protection for oligonucleotide synthesis investigated. The 2′-C-3′-O-γ-butyrolactone (5) was also shown to be a useful intermediate for the preparation of these analogues.

  已经制备了包含羧酸（2），伯酰胺（3）或伯羟基（4）的官能化的2'- C-支链核苷，并研究了它们对寡核苷酸合成的保护。还显示了2'- C- 3'- O - γ-丁内酯（5）是制备这些类似物的有用中间体。
• The Synthesis of 2′-C-Functionalised Nucleosides for Incorporation into Catalytic RNA
  作者：Anthony J. Lawrence、John B. J. Pavey、Ian A. O'Neil、Richard Cosstick

  DOI：10.1080/07328319708006215

  日期：1997.7

  Five 2'-C-functionalized nucleosides (1-5) have been prepared and incorporated into dinucleoside monophosphates. The effect of the functionality on the stability of the adjacent phosphodiester bond toward hydrolysis by nuclease enzymes and extremes of pH has been assessed.
• Synthesis and Properties of 2‘-Deoxy-2‘-α-<i>C</i>-branched Nucleosides and Nucleotides
  作者：Anthony J. Lawrence、John B. J. Pavey、Richard Cosstick、Ian A. O'Neil

  DOI：10.1021/jo9614607

  日期：1996.1.1

  Four functionalized 2'-deoxy-2'-alpha-C-branched nucleosides, namely, 2'-deoxy-2'-alpha-C-(carboxymethyl)-uridine, 2'-deoxy-2'-alpha-acetamidouridine, 2'-deoxy-2'-alpha-C-(hydroxyethyl)uridine, and 2'-deoxy-2'-alpha-C-(2,3-dihydroxypropyl)uridine, have been prepared. Conversion of these nucleosides to their appropriately protected phosphoramidites, followed by tetrazole-induced reaction with 2',3'-di-O-acetyluridine, oxidation, and subsequent deprotection furnished the corresponding dinucleoside monophosphates. During the oxidation of the amide-derived phosphite, partial dehydration occurred to give a mixture of the amide- and nitrile-containing dimers. Interestingly, the ratio of amide to nitrile could be largely controlled by choice of oxidant. The hydroxyethyl- and dihydroxypropyl-modified dimers were particularly resistant to snake venom phosphodiesterase-catalyzed hydrolysis (relative half-lives of 129 and 120, respectively, in comparison to UpU). It is anticipated that these nucleoside analogues will ultimately be used in the construction of ribozymes containing enhanced functionality and nuclease resistance.
• Lawrence, Anthony J.; Pavey, John B. J.; Chan, Mai-Yee, Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2761 - 2767
  作者：Lawrence, Anthony J.、Pavey, John B. J.、Chan, Mai-Yee、Fairhurst, Robin A.、Collingwood, Stephen P.、Fisher, Julie、Cosstick, Richard、O'Neil, Ian A.

  DOI：——

  日期：——
• Syntheses of 2′-C-amidoalkyl and 2′-C-cyanoalkyl containing oligodeoxyribonucleotides and assessment of their hybridisation affinity for complementary DNA and RNA
  作者：Lavinia Brennan、Richard Cosstick、Ian A. O'Neil、Arthur Van Aerschot

  DOI：10.1016/j.tet.2006.11.024

  日期：2007.1

  Oligodeoxynucleotides containing 2′-C-branched nucleosides with an amide or nitrile appended to either a one or two carbon alkyl chain have been synthesised. The phosphoramidites of the 2′-C-modified nucleosides were prepared and incorporated into the oligonucleotides using automated DNA synthesis. The duplex stability with complementary RNA and DNA was measured by UV melting experiments, in order

  合成了含有2'- C-支链核苷且酰胺或腈附接到一个或两个碳烷基链上的寡脱氧核苷酸。制备2'- C-修饰的核苷的亚磷酰胺，并使用自动DNA合成将其掺入寡核苷酸中。通过紫外熔解实验测量了具有互补RNA和DNA的双链体稳定性，以评估酰胺/腈功能是否可以在不存在2'-氧的情况下诱导任何双链体稳定性。在没有2'-氧的情况下，含有2'- C-修饰的寡核苷酸的双链体稳定性降低。