Rapoport's reagent | 82892-54-4

• 英文名称: Rapoport's reagent
• 英文别名: 1-(benzyloxycarbonyl)-3-ethylimidazolium tetrafluoroborate
• CAS: 82892-54-4
• 化学式: BF₄*C₁₃H₁₅N₂O₂
• 分子量: 318.079
• InChiKey: RKXVUBHPDZDZIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  Rapoport's reagent 在 lithium hydroxide 、 sodium hydroxide 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-((N⁶-(benzyloxycarbonyl)adenin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycine
  参考文献：
  名称：

  含有腺嘌呤或鸟嘌呤的肽核酸可识别互补DNA序列中的胸腺嘧啶和胞嘧啶

  摘要：

  制备用于引入G和A的肽核酸（PNA）单体构件，并将其用于合成HT 4 XT 5 -Lys-NH 2（X = G或A），通过T m测量显示以识别它们的互补性平行（N-末端PNA / 5'-DNA）和反平行模式的DNA序列；每种情况下的化学计量是（PNA）2 / DNA。

  DOI：

  10.1039/c39930000800
• 作为产物：
  描述：

  氯甲酸苄酯 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 Rapoport's reagent
  参考文献：
  名称：

  使用 N-（苄氧羰基）封闭的核苷合成寡脱氧核糖核苷酸

  摘要：

  2'-脱氧腺苷和 2'-脱氧胞苷的外氨基已被封闭为氨基甲酸苄酯，2'-脱氧鸟苷已被封闭为其 2-N-（苄氧羰基）氨基甲酸酯和 6-O-苄基醚。这些封闭的核苷已被纳入有效的寡脱氧核糖核苷酸合成方案中，并且所得寡聚体已通过使用转移氢化成功解封闭。去封闭条件不会导致嘧啶碱基减少。

  DOI：

  10.1021/ja00385a026

文献信息

• Mixed-sequence pyrrolidine-amide oligonucleotide mimics: Boc(Z) synthesis and DNA/RNA binding properties
  作者：Roberta J. Worthington、Adam P. O'Rourke、Jordi Morral、T. H. Samuel Tan、Jason Micklefield

  DOI：10.1039/b613386j

  日期：——

  Pyrrolidine-amide oligonucleotide mimics (POMs) exhibit promising properties for potential applications, including in vivo DNA and RNA targeting, diagnostics and bioanalysis. Before POMs can be evaluated in these applications it is first necessary to synthesise and establish the properties of fully modified oligomers, with biologically relevant mixed sequences. Accordingly, Boc-Z-protected thyminyl, adeninyl and cytosinyl POM monomers were prepared and used in the first successful solid phase synthesis of a mixed sequence POM, Lys-TCACAACTT-NH2. UV thermal denaturation studies revealed that the POM oligomer is capable of hybridising with sequence selectivity to both complementary parallel and antiparallel RNA and DNA strands. Whilst the duplex melting temperatures (Tm) were higher than the corresponding duplexes formed with isosequential PNA, DNA and RNA oligomers the rates of association/dissociation of the mixed sequence POM with DNA/RNA targets were noticeably slower.

  吡咯烷酰胺低聚核苷酸模拟物（POMs）展现出了有前景的特性，具有潜在的应用价值，包括体内DNA和RNA靶向、诊断和生物分析。在评估这些应用之前，首先需要合成并确定具有生物学相关混合序列的完全修饰低聚物的性质。因此，制备了Boc-Z保护的胸苷基、腺苷基和胞苷基POM单体，并首次成功用于混合序列POM（Lys-TCACAACTT-NH2）的固相合成。UV热变性研究表明，POM低聚物能够与互补的平行和反平行RNA及DNA链进行序列选择性杂交。尽管双链熔解温度（Tm）高于等序列PNA、DNA和RNA低聚物形成的双链，但混合序列POM与DNA/RNA靶标的结合/解离速率明显较慢。
• Synthesis of the monomeric building blocks of Z-olefinic PNA (Z-OPA) containing the bases adenine and thymine
  作者：Michel Cantin、Rolf Schütz、Christian J. Leumann

  DOI：10.1016/s0040-4039(97)00871-x

  日期：1997.6

  The synthesis of the Boc-protected Z-olefinic peptide nucleic acid analog (Z-OPA) monomers containing the base thymine 11 and Cbz-adenine 19 is described. Key step in the synthesis of the underlying carbon framework is a Pd(0)-catalyzed coupling of a vinyl iodide, prepared in three steps from 3-butynol, with the Reformatsky reagent derived from ethyl α-bromoacetate.

  描述了含有基本胸腺嘧啶11和Cbz-腺嘌呤19的Boc保护的Z-烯烃肽核酸类似物（Z- OPA）单体的合成。合成基础碳骨架的关键步骤是三步法从3-丁炔醇制备的碘化乙烯与Pformat（0）催化的Reformatsky试剂衍生自α-溴乙酸乙酯的偶联反应。
• Synthesis of benzyl and benzyloxycarbonyl base-blocked 2'-deoxyribonucleosides
  作者：Bruce E. Watkins、Henry Rapoport

  DOI：10.1021/jo00144a014

  日期：1982.11
• Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization
  作者：Kim L. Dueholm、Michael Egholm、Carsten Behrens、Leif Christensen、Henrik F. Hansen、Tore Vulpius、Kenneth H. Petersen、Rolf H. Berg、Peter E. Nielsen、Ole Buchardt

  DOI：10.1021/jo00098a042

  日期：1994.9

  The preparation of mixed-sequence PNAs (PNAs containing the four natural nucleobases; thymine, cytosine, adenine, and guanine) is described. The PNA monomers containing thymine, Cbz-protected cytosine, or adenine or benzyl-protected guanine were prepared via convergent syntheses. Subsequent to introduction of the carboxymethyl linker at N-1 of the pyrimidines or N-9 of the purines and suitable protection of exocyclic groups, the nucleobase derivatives were coupled to the Boc-protected backbone esters 10a or 10b and finally hydrolyzed affording the monomers 12a-d. The exocyclic amino groups of cytosine and adenine were protected with a benzyloxycarbonyl group. The exocyclic amino group of guanine was left unprotected whereas O-6 was protected as the benzyl ether. Two mixed-sequence 10-mers, each with five purines incorporated, and a mixed-sequence 15-mer Containing seven purines were assembled essentially following standard solid phase peptide synthesis protocols.
• Investigation, optimization and synthesis of sulfamoyloxy-linked aminoacyl-AMP analogues
  作者：Itedale Namro Redwan、Thomas Ljungdahl、Morten Grøtli

  DOI：10.1016/j.tet.2011.12.011

  日期：2012.2

  Aminoacyl-tRNA synthetases (aaRSs) constitute a family of enzymes that transfer amino acids to their corresponding tRNA molecules to form aminoacyl-tRNAs and have been validated as potential drug targets. Sulfamoyloxy-linked aminoacyl-AMP analogues are potent inhibitors of aaRSs. In this article, we report the synthesis of several new sulfamoyl analogues of as-AMP that up to now have been difficult or even impossible to prepare with current synthetic strategies. The developed synthetic strategy relies on performing the synthesis under neutral conditions followed by global deprotection using catalytic hydrogenation affording the desired 5'-0-(N-aminoacyl)sulfamoyladenosine compounds. (C) 2011 Elsevier Ltd. All rights reserved.