2'-O-carbamoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine | 1192821-15-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-carbamoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
• CAS: 1192821-15-0
• 化学式: C₂₂H₃₉N₃O₈Si₂
• 分子量: 529.738
• InChiKey: QNRPNABVBAINPF-VBSBHUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  144.1
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2'-O-carbamoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Uridine 2'-carbamate
  参考文献：
  名称：

  Synthesis and hybridization of 2′-O-methyl-RNAs incorporating 2′-O-carbamoyluridine and unique participation of the carbamoyl group in U–G base pair

  摘要：

  2'-O-Carbamoyluridine (U-cm) was synthesized and incorporated into DNAs and 2,-O-Me-RNAs. The oligonucleotides incorporating U-cm formed less stable duplexes with their complementary and U-cm-U, U-cm-C single-base mismatched DNAs and RNAs in comparison with those without the carbamoyl group. On the contrary, the T-m analyses revealed that the duplexes with a mismatched U-cm-G base pair showed almost the same thermostability as the corresponding unmodified duplexes. Molecular dynamics (MD) simulations of the U-cm-modified 2'-O-Me-RNA/RNA duplexes with U-cm-G mismatched base pair suggested that the carbamoyl group could participate in the U-cm-G base pair by an additional intermolecular hydrogen bond between the carbamoyl oxygen and the H2 of the guanine base. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.053
• 作为产物：
  描述：

  2'-O-phenoxycarbonyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine 在 吡啶 、 氨 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以89%的产率得到2'-O-carbamoyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine
  参考文献：
  名称：

  Synthesis and hybridization of 2′-O-methyl-RNAs incorporating 2′-O-carbamoyluridine and unique participation of the carbamoyl group in U–G base pair

  摘要：

  2'-O-Carbamoyluridine (U-cm) was synthesized and incorporated into DNAs and 2,-O-Me-RNAs. The oligonucleotides incorporating U-cm formed less stable duplexes with their complementary and U-cm-U, U-cm-C single-base mismatched DNAs and RNAs in comparison with those without the carbamoyl group. On the contrary, the T-m analyses revealed that the duplexes with a mismatched U-cm-G base pair showed almost the same thermostability as the corresponding unmodified duplexes. Molecular dynamics (MD) simulations of the U-cm-modified 2'-O-Me-RNA/RNA duplexes with U-cm-G mismatched base pair suggested that the carbamoyl group could participate in the U-cm-G base pair by an additional intermolecular hydrogen bond between the carbamoyl oxygen and the H2 of the guanine base. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.053

文献信息

• JP2015/20994
  申请人：——

  公开号：——

  公开（公告）日：——