4-amino-1-[(1s,3r,4r,7s)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]hept-3-yl]-5-methylpyrimidin-2(1h)one | 847650-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-1-[(1s,3r,4r,7s)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]hept-3-yl]-5-methylpyrimidin-2(1h)one
• 英文别名: 5-methyl-(2'-o,4'-C-methylene)-cytidine；2'-o,4'-C-methylene-5-methylcytidine；4-Amino-1-[(1s,3r,4r,7s)-7-Hydroxy-1-(Hydroxymethyl)-2,5-Dioxabicyclo[2.2.1]Hept-3-Yl]-5-Methylpyrimidin-2(1h)-One；4-amino-1-[(1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]-5-methylpyrimidin-2-one
• CAS: 847650-87-7
• 化学式: C₁₁H₁₅N₃O₅
• 分子量: 269.257
• InChiKey: NELYIRACPIJATH-SZVQBCOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-1-[(1s,3r,4r,7s)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]hept-3-yl]-5-methylpyrimidin-2(1h)one 在 磷酸三甲酯 、 三氯氧磷 、 三正丁胺 、 三丁基焦磷酸铵 、 三乙基碳酸氢铵缓冲液 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 8.02h， 以55%的产率得到
  参考文献：
  名称：

  Chemical Synthesis of LNA-mCTP and Its Application for MicroRNA Detection

  摘要：

  Locked nucleic acids (LNA) are being applied in hybridization studies, but current locked nucleotides cannot be transcribed into RNA probes. Here, the authors report the use of a new synthetic locked nucleotide, locMeCytidine-5'-triphosphate (LNA-mCTP), for hybridization study. This synthetic LNA-mCTP can be transcribed into a short (similar to 30-nt) RNA probe. Dot blot hybridization on nylon membrane suggested that the short P-33-LNA RNA probes had strong binding affinity to target oligonucleotides and its detection sensitivity was approximately similar to 1000 miRNAs in a 20- to 30-m (diameter) dot area. On tissue sections, the differential expression pattern of mir-124 within different tissue regions revealed by short P-33- LNA RNA probes correlated well to that analyzed by real-time RT-PCR. In addition, the specific cellular distribution of vasoactive intestinal polypeptide mRNAs in the mouse brain was the same using a 30-nt P-33-LNA RNA probe and a 1.5-kb P-33-RNA probe. These results suggested the high hybridization specificity of the small LNA-RNA probes to target small RNAs. Finally, the authors applied P-33-LNA probes to detect miRNA let-7C expression in human cancer tissues. Let-7C was clearly present in lung, prostate, and colon cancers but undetectable in ovary and thyroid cancer samples. These results suggested that this miRNA detection method provides an alternative tool to study the cellular distribution of miRNAs in tissues.

  DOI：

  10.1080/15257770701571693
• 作为产物：
  描述：

  (1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-methyl-4-N-benzoylcytosine-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以70%的产率得到4-amino-1-[(1s,3r,4r,7s)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]hept-3-yl]-5-methylpyrimidin-2(1h)one
  参考文献：
  名称：

  Chemical Synthesis of LNA-mCTP and Its Application for MicroRNA Detection

  摘要：

  Locked nucleic acids (LNA) are being applied in hybridization studies, but current locked nucleotides cannot be transcribed into RNA probes. Here, the authors report the use of a new synthetic locked nucleotide, locMeCytidine-5'-triphosphate (LNA-mCTP), for hybridization study. This synthetic LNA-mCTP can be transcribed into a short (similar to 30-nt) RNA probe. Dot blot hybridization on nylon membrane suggested that the short P-33-LNA RNA probes had strong binding affinity to target oligonucleotides and its detection sensitivity was approximately similar to 1000 miRNAs in a 20- to 30-m (diameter) dot area. On tissue sections, the differential expression pattern of mir-124 within different tissue regions revealed by short P-33- LNA RNA probes correlated well to that analyzed by real-time RT-PCR. In addition, the specific cellular distribution of vasoactive intestinal polypeptide mRNAs in the mouse brain was the same using a 30-nt P-33-LNA RNA probe and a 1.5-kb P-33-RNA probe. These results suggested the high hybridization specificity of the small LNA-RNA probes to target small RNAs. Finally, the authors applied P-33-LNA probes to detect miRNA let-7C expression in human cancer tissues. Let-7C was clearly present in lung, prostate, and colon cancers but undetectable in ovary and thyroid cancer samples. These results suggested that this miRNA detection method provides an alternative tool to study the cellular distribution of miRNAs in tissues.

  DOI：

  10.1080/15257770701571693

文献信息

• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。
• ADVANCED DRUG DEVELOPMENT AND MANUFACTURING
  申请人：Los Alamos National Security, LLC

  公开号：EP2084519A2

  公开（公告）日：2009-08-05
• X-RAY FLUORESCENCE ANALYSIS METHOD
  申请人：Los Alamos National Security, LLC

  公开号：EP2084519B1

  公开（公告）日：2012-08-01
• X-ray microscope
  申请人：XRpro Sciences, Inc.

  公开号：EP2511844B1

  公开（公告）日：2015-08-12
• MODIFIED NUCLEOSIDES, NUCLEOTIDES, AND NUCLEIC ACIDS, AND USES THEREOF
  申请人：Moderna Therapeutics, Inc.

  公开号：EP2763701B1

  公开（公告）日：2018-12-19