N⁶-[(2-cyanoethoxy)carbonyl]-2′-O-acetyladenosine | 1582752-92-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-[(2-cyanoethoxy)carbonyl]-2′-O-acetyladenosine
• 英文别名: [(2R,3R,4R,5R)-2-[6-(2-cyanoethoxycarbonylamino)purin-9-yl]-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 1582752-92-8
• 化学式: C₁₆H₁₈N₆O₇
• 分子量: 406.355
• InChiKey: ZLRBCEPSSVOEEF-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  182
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 N⁶-[(2-cyanoethoxy)carbonyl]-2′-O-acetyladenosine 、 N⁶-[(2-cyanoethoxy)carbonyl]-3′-O-acetyladenosine
  参考文献：
  名称：

  Solid-Phase Synthesis and Hybrization Behavior of Partially 2′/3′-O-Acetylated RNA Oligonucleotides

  摘要：

  Synthesis of partially 2'/3'-O-acetylated oligoribonucleotides has been accomplished by using a 2'/3'-O-acetyl orthogonal protecting group strategy in which nonnucleophilic strong-base (DBU) labile nucleobase protecting groups and a LTV-light cleavable linker were used. Strong-base stability of the photolabile linker allowed on-column nucleobase and phosphate deprotection, followed by a mild cleavage of the acetylated oligonucleotides from the solid support with UV light. Two 17nt oligonucleotides, which were synthesized possessing one specific internal 2' or 3'-acetyl group, were used as synthetic standards in a recent report from this laboratory detailing the prebiotically plausible ligation of RNA oligonucleotides. In order to further investigate the effect of 2'/3'-O-acetyl groups on the stability of RNA duplex structure, two complementary bis-acetylated RNA oligonucleotides were also expediently obtained with the newly developed protocols. UV melting curves of 2'-O-acetylated RNA duplexes showed a consistent similar to 3.1 degrees C decrease in T-m per 2'-O-acetyl group.

  DOI：

  10.1021/jo5002824