BZ-RC 亚磷酰胺单体 | 118380-84-0

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: BZ-RC 亚磷酰胺单体
• 中文别名: BZ-RC亚磷酰胺单体；Bz-rC亚磷酰胺单体
• 英文名称: N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)cytidine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
• 英文别名: 5'-dimethoxytrityl-N4-benzoylcytidine-2'-O-t-butyldimethylsilyl-3'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite；Bz-rC Phosphoramidite；N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 118380-84-0；131349-30-9；131349-36-5
• 化学式: C₅₂H₆₆N₅O₉PSi
• 分子量: 964.183
• InChiKey: VWNXEDLLHIFAOL-YOVDOAOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.47
• 重原子数：
  68
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  BZ-RC 亚磷酰胺单体 生成 [(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxyoxolan-3-yl] [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate;azane
  参考文献：
  名称：

  KIERZEK, RYSZARD;ROZEK, MAREK;MARKIEWICZ, WOJCIECH T., BULL. POL. ACAD. SCI. CHEM., 35,(1987) N 11-12, 507-516

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯甲酰-5'-O-[二(4-甲氧基苯基)苯甲基]-2'-O-[(1,1-二甲基乙基)二甲基硅]-胞苷 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以44%的产率得到BZ-RC 亚磷酰胺单体
  参考文献：
  名称：

  New nucleoside phosphoramidites and coupling protocols for solid-phase RNA synthesis

  摘要：

  The 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diethylphosphoramidites) 3, 5, 7, and 9, modified monomers for RNA synthesis, were prepared from 2-cyanoethyl N,N-diethylchloro-phosphoramidite (1). In conjunction with newly developed coupling protocols for automated solid-phase synthesis, they afforded synthetic oligoribonucleotides up to 74 base units in length. The performance of the new compounds was compared to the analogous 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) 4, 6, 8, and 10. Complete removal of benzoyl groups from N2-benzoylguanosine, which was incorporated into some of the synthetic oligoribonucleotides, was demonstrated. Purification procedures by reverse phase HPLC and PAGE methods are also presented.

  DOI：

  10.1021/jo00015a010

文献信息

• Synthesis of pCpCpA-3‘-<i>NH</i>-Phenylalanine as a Ribosomal Substrate
  作者：Biliang Zhang、Lei Zhang、Lele Sun、Zhiyong Cui

  DOI：10.1021/ol026560f

  日期：2002.10.1

  [reaction: see text] The trinucleotide cytidylyl(3'-->5'phosphoryl)cytidylyl(3'-->5'phosphoryl)-3'-deoxy-3'-(L-phenylalanyl) amido adenosine (CpCpA-NH-Phe) was synthesized by phosphoramidite chemistry from 3'-amino-3'-deoxyadenosine as the ribosomal substrate. The 3'-amino-3'-deoxyadenosine was first converted to 3'-(N-tert-butyloxycarbonyl-L-phenylalanine)amido-3'-deoxy-6-N,6-N,2'-O-tribenzoyl-adenosine

  [反应：见正文]三核苷酸胞嘧啶（3'-> 5'磷酸基）胞嘧啶（3'-> 5'磷酸基）-3'-脱氧-3'-（L-苯丙氨酰基）酰胺基腺苷（CpCpA-NH通过亚磷酰胺化学反应，以3'-氨基-3'-脱氧腺苷为核糖体底物，合成了-Phe）。首先将3'-氨基-3'-脱氧腺苷转化为3'-（N-叔丁氧基羰基-L-苯丙氨酸）酰胺基3'-脱氧-6-N，6-N，2'-O-三苯甲酰基-腺苷，然后与胞苷亚磷酰胺偶联生成完全保护的CpCpA-NH-Phe-Boc。除去所有保护基团后，获得标题产物，然后用（32）P进行放射性标记，得到pCpCpA-NH-Phe，对核糖体中的肽基转移酶反应显示出高活性。
• Preparation of Nucleotide Oligomer
  申请人：Jung Kyeong-Eun

  公开号：US20100273999A1

  公开（公告）日：2010-10-28

  The present invention provides a method for preparing nucleotide oligomers, including (a) coupling a nucleotide dimer or nucleotide trimer to a nucleoside attached to solid supports or to universal solid supports as a starting material; (b) sequentially coupling nucleotide monomers to the resulting structures of Step (a) to prepare a nucleotide oligomer; and (c) removing the nucleotide oligomers from the solid supports. The method of the present invention provides nucleotide oligomers having 15-20% higher purity than the conventional art. The present invention enables the efficient and inexpensive synthesis of nucleotide oligomers with high purity within a shorter period of time.

  本发明提供了一种制备核苷酸寡聚物的方法，包括(a)将核苷酸二聚体或核苷酸三聚体偶联到固相支撑上或通用固相支撑上的核苷酸作为起始物；(b)顺序地将核苷酸单体偶联到步骤(a)得到的结构上，制备核苷酸寡聚物；以及(c)从固相支撑上去除核苷酸寡聚物。本发明的方法提供了核苷酸寡聚物，其纯度比传统技术高出15-20%。本发明使得能够在较短时间内高效、廉价地合成高纯度的核苷酸寡聚物成为可能。
• Quick Access to Nucleobase-Modified Phosphoramidites for the Synthesis of Oligoribonucleotides Containing Post-Transcriptional Modifications and Epitranscriptomic Marks
  作者：Kamil Ziemkiewicz、Marcin Warminski、Radoslaw Wojcik、Joanna Kowalska、Jacek Jemielity

  DOI：10.1021/acs.joc.2c01390

  日期：2022.8.5

  nucleobases of commercially available nucleoside phosphoramidites. This method involves the deprotonation of amide groups under phase-transfer conditions and subsequent reaction with electrophilic molecules such as alkyl halides or organic isocyanates. Using this approach, we obtained 10 different classes of modified nucleoside phosphoramidites suitable for the synthesis of oligonucleotides, including several

  在这里，我们报告了一种简单的一步程序，用于修改市售核苷亚磷酰胺的核碱基中的N-亲核基团。该方法涉及在相转移条件下使酰胺基团去质子化，并随后与诸如烷基卤化物或有机异氰酸酯等亲电子分子反应。使用这种方法，我们获得了 10 种不同类型的适合合成寡核苷酸的修饰核苷亚磷酰胺，包括在天然 RNA 或 DNA 中发现的几种非规范核苷酸（例如，m 6 A、i 6 A、m 1 A、g 6 A、m 3 ℃，米4 ℃，米3 U，米1G 和 m 2 G)。核碱基的这种修饰是各种生物体中 RNA 稳定性和翻译活性的转录后调节的常见机制。为了更好地理解这一过程，必须识别和表征相关的细胞识别伙伴（例如蛋白质）。然而，这一步骤受到了对含有此类修饰核苷酸的分子工具的有限访问的阻碍。
• Phosphorylating Reagent-Free Synthesis of 5′-Phosphate Oligonucleotides by Controlled Oxidative Degradation of Their 5′-End
  作者：Corinne Sallamand、Audrey Miscioscia、Rémy Lartia、Eric Defrancq

  DOI：10.1021/ol300542s

  日期：2012.4.20

  The 5'-phosphorylated oligonucleotides (5'-pONs) are currently synthesized using expensive and sensitive modified phosphoramidite reagents. In this work, a simple, cost-effective, efficient, and automatable method is presented, based on the controlled oxidation of the 5'-terminal alcohol followed by a beta-elimination reaction. The latter reaction leads to the removal of the terminal 5'-nucleoside and subsequent formation of the 5'-phosphate moiety. Thus, chemical phosphorylation of oligonucleotides (DNA or RNA) is achieved without using modified phosphorarnidites.
• Kierzek, Ryszard; Rozek, Marek; Markiewicz, Wojciech T., Bulletin of the Polish Academy of Sciences: Chemistry, 1987, vol. 35, # 11-12, p. 507 - 516
  作者：Kierzek, Ryszard、Rozek, Marek、Markiewicz, Wojciech T.

  DOI：——

  日期：——