ethyl N-((N-⁴-(benzyloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate | 938175-07-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-((N-⁴-(benzyloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate
• 英文别名: Ethyl 2-[2-[4-(Cbz-amino)-2-oxopyrimidin-1(2H)-yl]-N-[2-(Boc-amino)ethyl]acetamido]acetate；ethyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl-[2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]acetate
• CAS: 938175-07-6
• 化学式: C₂₅H₃₃N₅O₈
• 分子量: 531.566
• InChiKey: DRKAAKUNURSKQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl N-((N-⁴-(benzyloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以69%的产率得到N-((N-⁴-(benzyloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Boc-aminoethyl)glycine
  参考文献：
  名称：

  Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization

  摘要：

  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.

  DOI：

  10.1021/jo00098a042
• 作为产物：
  描述：

  methyl (N⁴-benzyloxycarbonyl)cytosin-1-ylacetate 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl N-((N-⁴-(benzyloxycarbonyl)cytosin-1-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate
  参考文献：
  名称：

  Recognition of guanine and adenine in DNA by cytosine and thymine containing peptide nucleic acids (PNA)

  摘要：

  DOI：

  10.1021/ja00050a068

文献信息

• Recognition of guanine and adenine in DNA by cytosine and thymine containing peptide nucleic acids (PNA)
  作者：Michael Egholm、Peter E. Nielsen、Ole Buchardt、Rolf H. Berg

  DOI：10.1021/ja00050a068

  日期：1992.11
• 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.