4'-C-[N-(4-pentyn-1-yl)aminomethyl]thymidine | 1245703-97-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 4'-C-[N-(4-pentyn-1-yl)aminomethyl]thymidine
• CAS: 1245703-97-2
• 化学式: C₁₆H₂₃N₃O₅
• 分子量: 337.376
• InChiKey: KTKMCFGVGBQAEI-WOSRLPQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.14
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  116.58
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4'-C-[N-(4-pentyn-1-yl)aminomethyl]thymidine 在 吡啶 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphinyl]-4'-C-[N-methyl-N-(4-pentyn-1-yl)aminomethyl]-5'-O-(4,4'-dimethoxytrityl)thymidine
  参考文献：
  名称：

  Solid-Supported Synthesis and Click Conjugation of 4′-C-Alkyne Functionalized Oligodeoxyribonucleotides

  摘要：

  4'-C-[N,N-Di(4-pentyn-l-yl)aminomethyl]thymidine and 4'-C-[N-methyl-N-(4-pentyn-l-yl)aminomethyl]thymidine 3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidites (1, 2) were synthesized, and one or two such monomers were incorporated into a 15-mer oligodeoxyribonucleotide. After chain assembly, azido-functionalized ligands, including appropriate derivatives of 1,4-phenylenedimethaneamine, mannose, paromamine, and neomycin, were conjugated to the alkynyl groups by the click chemistry on a solid support. The influence of the 4'-modifications on the melting temperature with DNA and 2'-O-methyl RNA targets was studied. Oligonucleotides containing one to four mannose ligands in the central part of the chain (up to two 4'-C-[N,N-di(4-pentyn-l-yl)aminomethyl]thymidine units) form equally stable duplexes with complementary 2'-OMe RNA as the corresponding unmodified DNA sequence. At high salt content, the mannose conjugation is even stabilizing. On using a DNA target, a modest destabilization occurs. All the amino group bearing conjugates stabilized the duplexes, the DNA.DNA duplexes more than the DNA.2'-O-methyl RNA duplexes.

  DOI：

  10.1021/bc100268w
• 作为产物：
  描述：

  4'-C-aminomethyl-3'-O-(4,4'-dimethoxytrityl)thymidine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 22.0h， 生成 4'-C-[N-(4-pentyn-1-yl)aminomethyl]thymidine
  参考文献：
  名称：

  Solid-Supported Synthesis and Click Conjugation of 4′-C-Alkyne Functionalized Oligodeoxyribonucleotides

  摘要：

  4'-C-[N,N-Di(4-pentyn-l-yl)aminomethyl]thymidine and 4'-C-[N-methyl-N-(4-pentyn-l-yl)aminomethyl]thymidine 3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidites (1, 2) were synthesized, and one or two such monomers were incorporated into a 15-mer oligodeoxyribonucleotide. After chain assembly, azido-functionalized ligands, including appropriate derivatives of 1,4-phenylenedimethaneamine, mannose, paromamine, and neomycin, were conjugated to the alkynyl groups by the click chemistry on a solid support. The influence of the 4'-modifications on the melting temperature with DNA and 2'-O-methyl RNA targets was studied. Oligonucleotides containing one to four mannose ligands in the central part of the chain (up to two 4'-C-[N,N-di(4-pentyn-l-yl)aminomethyl]thymidine units) form equally stable duplexes with complementary 2'-OMe RNA as the corresponding unmodified DNA sequence. At high salt content, the mannose conjugation is even stabilizing. On using a DNA target, a modest destabilization occurs. All the amino group bearing conjugates stabilized the duplexes, the DNA.DNA duplexes more than the DNA.2'-O-methyl RNA duplexes.

  DOI：

  10.1021/bc100268w