5'-O-(tert-butyldiphenylsilyl)cytidine | 58479-65-5

• 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: 5'-O-(tert-butyldiphenylsilyl)cytidine
• 英文别名: TBDPS(-5)Ribf(b)-cytosin-1-yl；4-amino-1-[(2R,3R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyrimidin-2-one
• CAS: 58479-65-5
• 化学式: C₂₅H₃₁N₃O₅Si
• 分子量: 481.624
• InChiKey: OEXVFLPHVOLUNK-JMJGKCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  5'-O-(tert-butyldiphenylsilyl)cytidine 在 sodium periodate 、 ammonium biborate tetrahydrate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 7-O-(tert-butyldiphenylsilyl)-N-trityl morpholinocytidine
  参考文献：
  名称：

  由未保护的核糖核苷合成柔性保护的吗啉代单体的改进方案。

  摘要：

  已经开发了一种廉价且大大改进的方案，使用氧化乙二醇裂解和还原胺化策略从未保护的核糖核苷以高总收率合成受保护的吗啉代单体。与先前的方法不同，本策略允许在稍后的阶段安装环外胺保护剂，从而避免使用昂贵的或市售的环外胺保护的核糖核苷作为起始原料。为了证明本发明方法在选择保护基上的灵活性，已在环外胺位置用几个具有不同解嵌段性质的此类基团保护了单体。

  DOI：

  10.1080/15257770.2012.724491
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 胞苷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 5'-O-(tert-butyldiphenylsilyl)cytidine
  参考文献：
  名称：

  CMP-唾液酸缀合物的合成：用于酶促合成天然和设计的唾液酸寡糖的底物

  摘要：

  描述了CMP-NeuAc的几种同源物的合成。这些化合物是酶促糖基化的底物。

  DOI：

  10.1016/s0040-4020(97)00370-0

文献信息

• Synthesis and in vitro growth inhibitory activity of novel silyl- and trityl-modified nucleosides
  作者：Jenny-Lee Panayides、Véronique Mathieu、Laetitia Moreno Y. Banuls、Helen Apostolellis、Nurit Dahan-Farkas、Hajierah Davids、Leonie Harmse、M.E. Christine Rey、Ivan R. Green、Stephen C. Pelly、Robert Kiss、Alexander Kornienko、Willem A.L. van Otterlo

  DOI：10.1016/j.bmc.2016.04.036

  日期：2016.6

  Seventeen silyl- and trityl-modified (5'-O- and 3',5'-di-O-) nucleosides were synthesized with the aim of investigating the in vitro antiproliferative activities of these nucleoside derivatives. A subset of the compounds was evaluated at a fixed concentration of 100μM against a small panel of tumor cell lines (HL-60, K-562, Jurkat, Caco-2 and HT-29). The entire set was also tested at varying concentrations

  为了研究这些核苷衍生物的体外抗增殖活性，合成了十七个甲硅烷基和三苯甲基修饰的（5'-O-和3'，5'-di-O-）核苷。针对一小组肿瘤细胞系（HL-60，K-562，Jurkat，Caco-2和HT-29）以固定的100μM浓度评估了这些化合物的子集。还以两种人胶质瘤细胞株（U373和Hs683）的不同浓度对整套样品进行了测试，得出GI50值，最好的结果是〜25μM。
• Synthesis and Biophysical Properties of Triazole-Incorporated PMOs (TzPMOs): A Convergent, Click Ligation Approach
  作者：Arpan Banerjee、Arnab Das、Atanu Ghosh、Abhishek Gupta、Surajit Sinha

  DOI：10.1021/acs.joc.3c02242

  日期：2024.3.1

  The synthesis of phosphorodiamidate morpholino oligonucleotides (PMOs) incorporating single or double triazole rings in the backbone has been achieved via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The synthetic approach implemented is fundamentally convergent, involving the ligation of a 5′-azide PMO fragment to a 3′-alkyne fragment both in solution and on solid support. To access the 3′-alkyne

  通过 Cu(I) 催化的叠氮化物-炔环加成 (CuAAC) 合成了主链中包含单或双三唑环的磷酸二酰胺吗啉代寡核苷酸 (PMO)。所实施的合成方法基本上是收敛的，涉及在溶液中和固体支持物上将 5'-叠氮 PMO 片段与 3'-炔片段连接。为了获得 3'-炔 PMO 片段，我们合成了所有四种核碱基的 3'- N-炔丙基氯代氨基磷酸酯吗啉代单体。与常规类似物相比，所得的三唑掺入的 PMO (TzPMO) 对互补脱氧核糖核酸 (DNA)/核糖核酸 (RNA) 链表现出相当或改进的结合亲和力。最后，设计了一个全长 TzPMO 来靶向 Nanog 基因，与常规版本相比，表现出几乎相同的杂交特性。圆二色性研究揭示了 TzPMO 形成的双链体具有 B 型螺旋构象。
• Sproat, Brian S.; Beijer, Barbro; Groetli, Morten, Journal of the Chemical Society. Perkin transactions I, 1994, # 4, p. 419 - 432
  作者：Sproat, Brian S.、Beijer, Barbro、Groetli, Morten、Ryder, Ursula、Morand, Kenneth L.、Lamond, Angus I.

  DOI：——

  日期：——
• Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/jo000646+

  日期：2000.9.1

  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.
• Selective Inhibitors of Bacterial Phosphopantothenoylcysteine Synthetase
  作者：James D. Patrone、Jiangwei Yao、Nicole E. Scott、Garry D. Dotson

  DOI：10.1021/ja906537f

  日期：2009.11.18

  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.