N,2',3'-O-tribenzoylcytidine | 54898-05-4

• 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,2',3'-O-tribenzoylcytidine
• 英文别名: 2',3'-O,N⁴-tribenzoyl cytidine；[(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 54898-05-4
• 化学式: C₃₀H₂₅N₃O₈
• 分子量: 555.544
• InChiKey: YIIJQEOBNHKRCF-LYPBTDJXSA-N

物化性质

• 熔点：
  180-182 °C
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,2',3'-O-tribenzoylcytidine 在 氨基磺酰氯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以77%的产率得到2',3'-O,N(4)-tribenzoyl-5'-O-sulfamoyl cytidine
  参考文献：
  名称：

  Selective Inhibitors of Bacterial Phosphopantothenoylcysteine Synthetase

  摘要：

  Bacterial phosphopantothenotycysteine synthetase (PPCS) catalyzes the formation of phosphopantothenoylcysteine (PPC) from (R)-phosphopantothenate, L-cysteine, and cytidine-5'-triphosphate (CTP) and has been shown to be essential for growth and survival. The reaction proceeds through a phosphopantothenoyl cytidylate, mixed anhydride intermediate. Both structural and kinetic characterization studies on PPCS have shown differences in the nucleobase binding site between the bacterial and human enzyme. We report for the first time the design and synthesis of mimics of the phosphopantothenoyl cytidylate, which proved to be potent inhibitors of PPCS. These compounds were evaluated in vitro against PPCS from human and several species of bacteria and showed marked selectivity (up to 1000-fold) toward the bacterial. enzymes. A phosphodiester intermediate mimic was the most potent of the compounds synthesized and displayed stow-onset, tight-binding kinetics toward E. faecalis PPCS.

  DOI：

  10.1021/ja906537f
• 作为产物：
  描述：

  胞苷 在 咪唑 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 N,2',3'-O-tribenzoylcytidine
  参考文献：
  名称：

  Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid

  摘要：

  alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.

  DOI：

  10.1021/jo000646+

文献信息

• Novel Synthetic Approach to Multibenzoylated Nucleosides
  作者：Xue‐Feng Zhu、A. Ian Scott

  DOI：10.1080/00397910801916280

  日期：2008.4

  Abstract An improved and highly efficient synthetic approach to multibenzoylated nucleosides bearing free 5′‐hydroxyl groups is described here. By employing t-butyldimethylsilyl (TBDMS) rather than the more commonly used dimethoxytrityl (DMTr) as a temporary 5′‐OH protecting group of the starting nucleoside, this methodology provides the expected products in nearly quantitative yields, thereby substantially

  摘要 这里描述了一种改进的、高效的带有游离 5'-羟基的多苯甲酰化核苷的合成方法。通过使用叔丁基二甲基甲硅烷基 (TBDMS) 而不是更常用的二甲氧基三苯甲基 (DMTr) 作为起始核苷的临时 5'-OH 保护基团，该方法以接近定量的产率提供了预期的产品，从而大大降低了成本和工作量的合成。
• Phosphoramidate Dinucleosides as Hepatitis C Virus Polymerase Inhibitors
  作者：Ivan Zlatev、Hélène Dutartre、Ivan Barvik、Johan Neyts、Bruno Canard、Jean-Jacques Vasseur、Karine Alvarez、François Morvan

  DOI：10.1021/jm800617c

  日期：2008.9.25

  GC dinucleosides exhibiting a phosphoramidate internucleosidic linkage with neutral, amphiphile, positively or negatively charged side chains were synthesized. Their potential inhibitory effect on the hepatitis C virus (HCV) NS5B polymerase was evaluated in vitro and in HCV replicon containing cells. Whereas the amphiphile and the positively charged analogues were found to be inactive, the neutral

  合成了表现出与中性、两亲性、带正电或带负电的侧链的氨基磷酸酯核苷间键合的GC二核苷。在体外和在含有 HCV 复制子的细胞中评估了它们对丙型肝炎病毒 (HCV) NS5B 聚合酶的潜在抑制作用。虽然发现两亲物和带正电的类似物是无活性的，但当作为非对映异构体混合物进行测试时，中性 (1) 和带负电 (4) 的类似物会抑制酶活性。最有效的抑制剂被证明是带有羧基侧链的 5'-硫代磷酸化二核苷酸的 Sp 异构体 (8)（体外 IC 50 为 25 microM，在 HCV 亚基因组复制子中 EC 50 为 9 microM）。
• Stereochemistry of Internucleotide Bond Formation by the H-Phosphonate Method. 1. Synthesis and ³¹P Nmr Analysis of 16 Diribonulceoside (3′-5′)-H-Phosphonates and the Corresponding Phosphorothioates
  作者：Michal Sobkowski、Jadwiga Jankowska、Adam Kraszewski、Jacek Stawinski

  DOI：10.1080/15257770500265729

  日期：2005.9.1

  Sixteen diribonucleoside (3′-5′)-H-phosphonates were synthesized via condensation of the protected ribonucleoside 3′-H-phosphonates with nucleosides, and the influence of a nucleoside sequence on the observed stereoselectivity was analyzed. 31P NMR spectroscopy was used to evaluate a relationship between chemical shift and absolute configuration at the phosphorous center of the H-phosphonate diesters

  通过受保护的核糖核苷 3'-H-膦酸酯与核苷的缩合合成了 16 种二核糖核苷 (3'-5')-H-膦酸酯，并分析了核苷序列对观察到的立体选择性的影响。31P NMR光谱用于评估H-膦酸二酯以及相应硫代磷酸二酯的磷中心的化学位移和绝对构型之间的关系。尽管在大多数情况下发现了这种相关性，但也有一些例外，即由 RP 和 SP 非对映异构体产生的共振的相对位置颠倒的规则。
• 1,1,1,3,3,3-Hexafluoro-2-propyl group as a new phosphate protecting group for oligoribonucleotide synthesis in the phosphotriester approach
  作者：Shunichi Yamakage、Masayo Fujii、Hiroshi Takaku、Masaru Uemura

  DOI：10.1016/s0040-4020(01)89492-8

  日期：——

  The 1,1,1,3,3,3-Hexafluoro-2-propyl group can be used as a new class of phosphate protecting group for the protecting group of internucleotidic bonds in the oligonucleotide synthesis by the phosphotriester approach. This protecting group is removed easily by treatment with 0.3 M N1,N1,N3,N3-tetramethylguanidinium syn-2-pyridine-aldoximate in pyridine-water (9:1, v/v). The butylthio-carbonyl group was

  1,1,1,3,3,3-六氟-2-丙基可以用作一类新型的磷酸保护基，用于通过磷酸三酯法合成寡核苷酸中的核苷酸间键的保护基。通过在吡啶-水（9∶1，v / v）中用0.3MN 1，N 1，N 3，N 3-四甲基胍合-2-吡啶-醛糖酸处理容易地除去该保护基。选择丁基硫代羰基作为鸟苷的O 6-酰胺和N 2-氨基官能团和尿苷的N 3-酰亚胺基团的保护基。完全保护的单体单元（）是通过磷酸化剂（）与。这些单体单元已成功用于合成四膜虫的r-RNA前体的盒9R序列UGUCGGUC。
• Chemical Synthesis of Branched Oligoribonucleotides
  作者：Mitsuo Sekine、Jarmo Heikkilä、Tsujiaki Hata

  DOI：10.1246/bcsj.64.588

  日期：1991.2

  This paper describes the full detail of the chemical synthesis of branched oligoribonucleotides by use of appropriately protected adenosine 2′,3′-diphosphate derivatives (13 and 30), as key intermediates, which were synthesized by a series of reactions involving phosphoryl rearrangement via a new phosphorylation process. Branched triribonucleotides ApCpG (21) and ApUpG (27) were obtained by using the

  本文描述了通过使用适当保护的腺苷 2',3'-二磷酸衍生物（13 和 30）作为关键中间体，通过一系列涉及磷酰基重排的反应合成的支链寡核糖核苷酸的完整细节。新的磷酸化过程。通过使用合成单元 13 获得了支链三核糖核苷酸 ApCpG (21) 和 ApUpG (27)。讨论了这些合成过程中的几个问题。使用 30 作为改进的构建单元使我们能够制备中性的合成中间体，即完全酯化的物质，这允许在支链六核糖核苷酸衍生物 CpUpGpApCpG 的整个合成过程中通过硅胶柱薄层色谱法轻松纯化它们。