Uridine 2'-carbamate | 89998-91-4

• 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: Uridine 2'-carbamate
• 英文别名: 2'-O-carbamoyluridine；[(2R,3R,4R,5R)-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] carbamate
• CAS: 89998-91-4
• 化学式: C₁₀H₁₃N₃O₇
• 分子量: 287.229
• InChiKey: FAVUEIJXZZABCR-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 Uridine 2'-carbamate 在 吡啶 、 二氯乙酸 、 三乙胺 作用下， 反应 23.0h， 以5.5 g的产率得到2'-O-carbamoyl-5'-O-(4,4'-dimethoxytrityl)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
• 作为产物：
  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

文献信息

• Bicyclic Compounds and Their Use
  申请人：Fairlamb Ian

  公开号：US20090299049A1

  公开（公告）日：2009-12-03

  The present invention provides fluorescent bicyclic compounds of the formula (I); wherein ring A, the broken lines -----, C 1 ----C 2 , R 4 and R 1 are as defined herein. The invention also relates to nucleoside and nucleotide analogues of said compounds, and their use as biological markers.

  本发明提供了式(I)的荧光双环化合物，其中环A，断裂的线-----，C1----C2，R4和R1如本文所定义。本发明还涉及该化合物的核苷和核苷酸类似物，以及它们作为生物标记物的用途。
• Reaction of uridine and uridine 5'-phosphate with diiminosuccinonitrile and cyanogen bromide in aqueous solution. Direct synthesis of the 2,2'-anhydronucleoside linkage at 2.degree.C
  作者：J. P. Ferris、H. Yanagawa

  DOI：10.1021/jo00186a008

  日期：1984.6
• BICYCLIC COMPOUNDS AND THEIR USE
  申请人：THE UNIVERSITY OF YORK

  公开号：EP1984455A2

  公开（公告）日：2008-10-29
• [EN] BICYCLIC COMPOUNDS AND THEIR USE<br/>[FR] COMPOSES BICYCLIQUES ET LEUR UTILISATION
  申请人：UNIV YORK

  公开号：WO2007091056A2

  公开（公告）日：2007-08-16

  [EN] The present invention provides fluorescent bicyclic compounds of the formula (I); wherein ring A, the broken lines -----, C₁----C₂, R⁴ and R¹ are as defined herein. The invention also relates to nucleoside and nucleotide analogues of said compounds, and their use as biological markers.
  [FR] La présente invention concerne des composés bicycliques fluorescents appartenant à la formule (I) : dans laquelle le composé cyclique A, les lignes en pointillé -----, C₁----C₂, R⁴ et R¹ sont tels que définis par celle-ci. L'invention se rapporte également aux analogues de nucléosides et de nucléotides desdits composés et à leur utilisation en tant que marqueurs biologiques.
• Synthesis and hybridization of 2′-O-methyl-RNAs incorporating 2′-O-carbamoyluridine and unique participation of the carbamoyl group in U–G base pair
  作者：Kohji Seio、Ryuya Tawarada、Takeshi Sasami、Masashi Serizawa、Misako Ise、Akihiro Ohkubo、Mitsuo Sekine

  DOI：10.1016/j.bmc.2009.08.053

  日期：2009.10

  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.