2-eelenouridine | 40555-29-1

• 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: 2-eelenouridine
• 英文别名: 2-selenouridine；2-seleno-uridine；2-Selenouridin；2-Selenuridin
• CAS: 40555-29-1
• 化学式: C₉H₁₂N₂O₅Se
• 分子量: 307.165
• InChiKey: RFZIZXWYWPNBGL-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.51
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  107.71
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-eelenouridine 在 吡啶 、 氟化氢吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 5′-O-(4,4′-dimetoxytrityl)-2′-O-tert-butyldimethylsilyl-2-selenouridine
  参考文献：
  名称：

  An Efficient Synthesis of 2-Selenouridine and Its Phosphoramidite Precursor

  摘要：

  We describe an efficient and scalable synthetic route to the natural occurring 2-selenouridine ((SeU)-U-2) and its suitably protected derivative for phosphoramidite synthesis. From known fully TBDMS-protected thiouridine, the corresponding selenouridine was synthesized via the reaction of methylthiouridine with NaHSe, which was then completely deprotected without affecting the selenocarbonyl moiety to deliver (SeU)-U-2. Next, (SeU)-U-2 was converted into the 2'-O-TBDMS-5'-O-DMT derivative in 81% yield over four steps including di-tert-butylsilylene (DTBS) introduction at O3' and O5', O2'-silylation, selective cleavage of DTBS, and DMT introduction. This synthetic route enabled gram-scale preparation of both (SeU)-U-2 and its phosphoramidite precursor in excellent yields. Furthermore, the predicted C3'-endo conformational preference of (SeU)-U-2 was experimentally confirmed by NMR spectroscopy.

  DOI：

  10.3987/com-15-13349
• 作为产物：
  描述：

  四乙酰核糖 在 咪唑 、 硫酸氢铵 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 四丁基氟化铵 、 selenium 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 六甲基二硅氮烷 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 117.5h， 生成 2-eelenouridine
  参考文献：
  名称：

  [EN] MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF
  [FR] MOLÉCULES D'ACIDE NUCLÉIQUE MODIFIÉES ET LEURS UTILISATIONS

  摘要：

  本公开提供了经修改的核苷、核苷酸和核酸，以及它们的使用方法。

  公开号：

  WO2014093924A1

文献信息

• Optimized Biocatalytic Synthesis of 2‐Selenopyrimidine Nucleosides by Transglycosylation**
  作者：Katja F. Hellendahl、Felix Kaspar、Xinrui Zhou、Zhaoyi Yang、Zhen Huang、Peter Neubauer、Anke Kurreck

  DOI：10.1002/cbic.202100067

  日期：2021.6.2

  Se for yourself: We present a biocatalytic synthesis of selenium-containing pyrimidine nucleosides. Optimization of the reaction conditions improved the solubility and stability of the sensitive starting materials as well as previously observed low conversions. This approach offers a concise alternative to traditionally employed multistep routes to these compounds.

  Se for myself：我们提出了含硒嘧啶核苷的生物催化合成。反应条件的优化提高了敏感起始材料的溶解度和稳定性以及之前观察到的低转化率。这种方法为这些化合物的传统采用的多步骤路线提供了一种简洁的替代方案。
• [EN] ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF<br/>[FR] MOLÉCULES D'ACIDE NUCLÉIQUE ALTERNATIVES ET LEURS UTILISATIONS
  申请人：MODERNA THERAPEUTICS INC

  公开号：WO2015196130A3

  公开（公告）日：2016-03-03
• Alternative nucleic acid molecules and uses thereof
  申请人：Moderna Therapeutics, Inc.

  公开号：EP2918275B1

  公开（公告）日：2016-05-18
• Transformation of a wobble 2-thiouridine to 2-selenouridine via S-geranyl-2-thiouridine as a possible cellular pathway
  作者：Paulina Bartos、Anna Maciaszek、Anna Rosinska、Elzbieta Sochacka、Barbara Nawrot

  DOI：10.1016/j.bioorg.2014.05.012

  日期：2014.10

  The newly discovered S-geranylated 2-thiouridines (geS2U) (Dumelin et al., 2012) and 2-selenouridines (Se2U) were recently shown to be synthesized by a single enzyme (selenouridine synthase, SelU) through two distinct pathways using the same 2-thiouridine substrate (S2U); however, no clear catalytic mechanism was proposed. We suggest that S-geranyl-2-thiouridine is an intermediate of the SelU-catalyzed conversion of S2U to Se2U. The successful chemical transformation of S2U -> geS2U -> Se2U is demonstrated here as an initial approximation of the intracellular pathway. The structure of Se2U was confirmed by spectroscopic methods, which included, for the first time, Se-77 NMR data (delta 354 ppm). (C) 2014 Elsevier Inc. All rights reserved.
• [EN] MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF<br/>[FR] MOLÉCULES D'ACIDE NUCLÉIQUE MODIFIÉES ET LEURS UTILISATIONS
  申请人：MODERNA THERAPEUTICS INC

  公开号：WO2014093924A1

  公开（公告）日：2014-06-19

  The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

  本公开提供了经修改的核苷、核苷酸和核酸，以及它们的使用方法。