3'-O-Acetyl-4-N-phenylacetyl-2'-deoxycytidine | 203986-36-1

• 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: 3'-O-Acetyl-4-N-phenylacetyl-2'-deoxycytidine
• CAS: 203986-36-1
• 化学式: C₁₉H₂₁N₃O₆
• 分子量: 387.392
• InChiKey: KSNUTNABTLAUDJ-HDMKZQKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  119.75
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3'-O-Acetyl-4-N-phenylacetyl-2'-deoxycytidine 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 18.17h， 生成 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-serine methyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Nucleopeptides

  摘要：

  Nucleoproteins, in which the hydroxy group of a serine, a threonine, or a tyrosine, is linked through a phosphodiester group to the 3'- or 5'-end of DNA or RNA, play decisive roles in important biological processes. They may even have a major part in the process of viral replication by nucleoprotein-primed elongation of the oligonucleotide strand. For the study of the biological phenomena, in which nucleoproteins are involved, nucleopeptides with the characteristic linkage between the peptide chain and the oligonucleotide of their parent nucleoproteins may serve as powerful tools. However, the synthesis of these compounds is complicated by their pronounced acid- and base-lability, as well as their multifunctionality. As a result, protecting groups, which can be removed under the mildest conditions, are required. For the construction of such peptide conjugates using a flexible building block strategy, a combination of enzyme-labile and chemical protecting groups was developed. The C-terminal blocking function can be removed selectively from fully protected nucleoamino acid methyl, 2-methoxyethyl (ME), and methoxyethoxyethyl (MEE) esters by saponification of the esters. After elongation of the peptide chain with amino acid or peptide methyl, ME, MEE, and choline esters, the C-terminal ester blocking group can again be removed easily. The methyl, ME, and MEE esters are cleaved off with lipase, and the choline ester group is selectively attacked by butyrylcholine esterase. The nucleoamino acids and peptides formed may be fully deprotected. To this end, the enzyme-labile N-phenylacetyl (PhAc) group, which was employed to mask the amino functions of the nucleobases, was removed. The O-acetate in the deoxyribose was saponified, and the allyl protecting groups present were cleaved by Pd-0-mediated allyl transfer. By combination of these techniques, a nucleopeptide was produced, which represents the characteristic linkage region of the nucleoprotein of adenovions 2. The conditions, under which the enzymatic deprotections proceed, are so mild that no undesired side reaction is observed, that is no depurination or beta elimination of the nucleosides occurs. In addition, the specificity of the biocatalysts ensures that the peptide bonds and the other protecting groups present are not attacked either.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<669::aid-chem669>3.0.co;2-v
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 1-羟基苯并三唑 、 zinc dibromide 作用下， 以 吡啶 、 硝基甲烷 、 乙腈 为溶剂， 反应 0.17h， 生成 3'-O-Acetyl-4-N-phenylacetyl-2'-deoxycytidine
  参考文献：
  名称：

  An enzymatic protecting group strategy for the synthesis of nucleopeptides

  摘要：

  Enzymatic protecting group techniques are used for the selective synthesis of acid-and base labile multifunctional nucleopeptides under mild conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10873-5

文献信息

• Chemoenzymatic synthesis of nucleopeptides
  作者：Herbert Waldmann

  DOI：10.1039/a704215i

  日期：——

  Acid- and base-labile multifunctional nucleopeptides have been selectively constructed under mild conditions by means of enzymatic protecting group techniques.

  通过酶保护基技术，我们在温和的条件下选择性地构建出了酸性和碱式失效的多功能核肽。