2'-O-carbamoyl-5'-O-(4,4'-dimethoxytrityl)uridine | 1192821-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2'-O-carbamoyl-5'-O-(4,4'-dimethoxytrityl)uridine
• 英文别名: H2NCO(-2)[DMT(-5)]Ribf(b)-uracil-1-yl；[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] carbamate
• CAS: 1192821-16-1
• 化学式: C₃₁H₃₁N₃O₉
• 分子量: 589.602
• InChiKey: IUFQADCJRCYOGX-YULOIDQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-carbamoyl-5'-O-(4,4'-dimethoxytrityl)uridine 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以99%的产率得到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 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 41.0h， 生成 2'-O-carbamoyl-5'-O-(4,4'-dimethoxytrityl)uridine
  参考文献：
  名称：

  JP2015/20994

  摘要：

  公开号：

文献信息

• Enzymatic synthesis and reverse transcription of RNAs incorporating 2′-O-carbamoyl uridine triphosphate
  作者：Yoshiaki Masaki、Hyugo Ito、Yuki Oda、Kazufumi Yamazaki、Nobuhiro Tago、Kentaro Ohno、Nozomi Ishii、Hirosuke Tsunoda、Takashi Kanamori、Akihiro Ohkubo、Mitsuo Sekine、Kohji Seio

  DOI：10.1039/c6cc05796a

  日期：——

  nzymatic synthesis and the reverse transcription of RNAs containing 2´-O-carbamoyl uridine were evaluated. A mild acidic deprotection procedure allowed the synthesis of 2´-O-carbamoyl uridine triphosphate (UcmTP). UcmTP was incorporated correctly...

  评估了含有2′-O-氨基甲酰基尿苷的RNA的酶促合成和逆转录。温和的酸性脱保护程序可以合成2′-O-氨基甲酰基尿苷三磷酸（UcmTP）。UcmTP已正确合并...