伪异胞苷 | 57100-18-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 伪异胞苷
• 英文名称: pseudoisocytidine
• 英文别名: 2-amino-5-β-D-ribofuranosyl-3H-pyrimidin-4-one；2-amino-5-(β-D-ribofuranosyl)-4(1H)-pyrimidinone；2-amino-5-(β-D-ribofuranosyl)pyrimidin-4-one；Pseudoisocytidin (β-Isomer)；Pseudoisocytidin；ψ-isocytidine；2-amino-5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-6-one
• CAS: 57100-18-2
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: MPDKOGQMQLSNOF-GBNDHIKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  伪异胞苷 在 乙酸酐 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 以3.2 g (85%)的产率得到假尿苷
  参考文献：
  名称：

  Nucleic acid labeling compounds

  摘要：

  揭示了含有杂环衍生物的核酸标记化合物。还公开了制备这种杂环化合物的方法。这些标记化合物适用于通过酶的附着，无论是末端还是内部，提供核酸检测的机制。

  公开号：

  US20050003496A1
• 作为产物：
  描述：

  2-Amino-4-chlor-5-(β-D-ribofuranosyl)-pyrimidin 在 sodium acetate 作用下， 以 水 为溶剂， 生成 伪异胞苷
  参考文献：
  名称：

  2,4-Dichloro-5-(.beta.-D-ribofuranosyl) pyrimidines and substituted

  摘要：

  一种C-核苷化合物，2,4-二氯-5-(2,3,5-三-O-乙酰基-β-D-核糖呋喃糖基)嘧啶，可用作合成具有抗肿瘤、抗病毒和/或抗菌活性的各种C-核苷化合物的主要起始物质。其结构式如下：##STR1## 2,4-二氯取代基位于杂环上，糖类活性位点被阻断，提供了适用于各种亲核取代的中间体化合物。这些方法产生了几种新型的RNA中已知的嘧啶核苷化合物的类似物，以及其他已经展示出化疗效用的化合物。

  公开号：

  US04092472A1

文献信息

• Synthesis of Pyridine, Pyrimidine and Pyridinone <i>C</i>-Nucleoside Phosphoramidites for Probing Cytosine Function in RNA
  作者：Jun Lu、Nan-Sheng Li、Selene C. Koo、Joseph A. Piccirilli

  DOI：10.1021/jo9016919

  日期：2009.11.6

  structures of the HDV ribozyme a cytosine nucleobase resides at the active site poised to participate directly in catalysis. Defining the functional role of the nucleobase requires nucleoside analogues that perturb the functional groups in a strategic manner. Herein, we have developed efficient methods for the synthesis of five C-nucleoside phosphoramidite derivatives that, when used in combination, provide

  在HDV核酶的结构中，胞嘧啶核碱基位于准备直接参与催化的活性位点。定义核碱基的功能作用需要以策略方式干扰功能基团的核苷类似物。在本文中，我们已经开发出了用于合成五种C-核苷亚磷酰胺衍生物的有效方法，这些方法结合使用时，可提供策略来探测胞嘧啶酮基和亚氨基氮的潜在功能。以11个步骤合成了亚磷酰胺15a和15b，从2-氨基-5-溴嘧啶（1a）和2-氨基-5-溴吡啶（1b）开始），总产量分别为10.8％和6.6％。从中间体11b以七个步骤制备亚磷酰胺21，总产率为33.7％。亚磷酰胺23和25分别由2,4-二氨基-5-（β- d-核呋喃糖基）-1,3-嘧啶（22）和假异胞苷（24）制备，总收率为15.9％（六步）和37.9％（四个步骤）。通过固相合成将这些亚磷酰胺掺入寡核苷酸中。
• Biochemical Detection of Cytidine Protonation within RNA
  作者：Adegboyega K. Oyelere、Scott A. Strobel

  DOI：10.1021/ja001918t

  日期：2000.10.1

  Perturbation of active site functional group pK(a)s is an important strategy employed by protein enzymes to achieve catalysis. There is increasing evidence to indicate that RNAs also utilize functional group pK(a) perturbation for folding and reactivity. one of the best candidates for a functionally relevant pK(a) perturbation is the N3 of C (pK(a) 4.2), which could be sufficiently raised to allow protonation near physiological pH. Here we report the synthesis and use of a series of alpha -phosphorothioate tagged cytidine analogues whose altered N3 pK(a)s make it possible to efficiently detect functionally relevant protonation events by nucleotide analogue interference mapping. 6-Azacytidine (n(6)C alphaS) and 5-fluorocytidine (f(5)C alphaS) both have enhanced acidity at the N3 position (pK(a) 2.6 and 2.3, respectively) but leave the hydrogen bonding face of C otherwise unaffected. In contrast, pseudoisocytidine (Psi iC alphaS) is a charge neutral analogue that mimics the hydrogen bonding character of protonated C. To test the utility of these analogues, we characterized the C300(+)-G97-C277 mutant form of the Tetrahymena group I intron, which is predicted to require C300 protonation for ribozyme folding and reactivity. At neutral to alkaline pHs, C300 was the only site of n(6)C alphaS and f(5)C alphaS interference within the intron, yet both interferences were rescued at acidic pH. Furthermore,Psi iC alphaS substitution at C300 resulted in enhanced activity at alkaline pHs, consistent with the presence of an N3 proton under the pH conditions studied. Interference mapping with these analogues provides an efficient and sensitive means to identify every site within an RNA where cytidine protonation is important for RNA function and may make it possible to identify C's that participate in general acid/base catalysis within ribozyme active sites.
• Reichman,U. et al., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 933 - 935
  作者：Reichman,U. et al.

  DOI：——

  日期：——
• OLIGONUCLEOTIDE PROBES BEARING QUENCHABLE FLUORESCENT LABELS, AND METHODS OF USE THEREOF
  申请人：Bayer Corporation

  公开号：EP1009852A2

  公开（公告）日：2000-06-21
• PURIFICATION OF OLIGOMERS USING DUAL-END SELECTION
  申请人：Bayer Corporation

  公开号：EP1105404A1

  公开（公告）日：2001-06-13