鸟苷5'-硫代二磷酸酯 | 71783-24-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 鸟苷5'-硫代二磷酸酯
• 英文名称: Guanosine 5'-O-(1-thiodiphosphate)
• 英文别名: [[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl] dihydrogen phosphate
• CAS: 71783-24-9；77481-24-4
• 化学式: C₁₀H₁₅N₅O₁₀P₂S
• 分子量: 459.27
• InChiKey: BMFDWNNPPWNUAM-PIORMBHWSA-N

物化性质

• 密度：
  2.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  263
• 氢给体数：
  7
• 氢受体数：
  12

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38

文献信息

• SYNTHESIS AND USE OF ANTI-REVERSE PHOSPHOROTHIOATE ANALOGS OF THE MESSENGER RNA CAP
  申请人：Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College

  公开号：EP2167523A2

  公开（公告）日：2010-03-31
• Synthesis and Use of Anti-Reverse Phosphorothioate Analogs of the Messenger RNA Cap
  申请人：Jemielity Jacek

  公开号：US20100233757A1

  公开（公告）日：2010-09-16

  New RNA cap analogs are disclosed containing one or more phosphorothioates groups. The analogs also contain modifications at the 2′-O position of 7-methylguanosine that prevent them from being incorporated in the reverse orientation during in vitro synthesis of mRNA and that hence are “anti-reverse cap analogs” (ARCAs). The ARCA modification ensures that the S atom is precisely positioned within the active sites of cap-binding proteins in both the translational and decapping machinery. The new S-ARCA analogs are resistant to in vivo decapping enzymes. Some S-ARCAs have a higher affinity for eIF4E than the corresponding analogs not containing a phosphorothioate group. When mRNAs containing the various S-ARCAs are introduced into cultured cells, some are translated as much as five-fold more efficiently than mRNAs synthesized with the conventional analog m 7 GpppG.
• US8153773B2
  申请人：——

  公开号：US8153773B2

  公开（公告）日：2012-04-10
• [EN] SYNTHESIS AND USE OF ANTI-REVERSE PHOSPHOROTHIOATE ANALOGS OF THE MESSENGER RNA CAP<br/>[FR] SYNTHÈSE ET UTILISATION D'ANALOGUES DE PHOSPHOROTHIOATE ANTI-INVERSE DE LA COIFFE D'ARN MESSAGER
  申请人：UNIV LOUISIANA STATE

  公开号：WO2008157688A2

  公开（公告）日：2008-12-24

  [EN] New RNA cap analogs are disclosed containing one or more phosphorothioates groups. The analogs also contain modifications at the 2'-O position of 7-methylguanosine that prevent them from being incorporated in the reverse orientation during in vitro synthesis of mRNA and that hence are "anti-reverse cap analogs" (ARCAs). The ARCA modification ensures that the S atom is precisely positioned within the active sites of cap-binding proteins in both the translational and decapping machinery. The new S-ARCA analogs are resistant to in vivo decapping enzymes. Some S-ARCAs have a higher affinity for eIF4E than the corresponding analogs not containing a phosphorothioate group. When mRNAs containing the various S-ARCAs are introduced into cultured cells, some are translated as much as five¬ fold more efficiently than mRNAs synthesized with the conventional analog m7GpppG.
  [FR] L'invention concerne de nouveaux analogues de coiffe d'ARN comprenant un ou plusieurs groupes phosphorothioate. Les analogues peuvent également contenir des modifications en position 2'-O de la 7-méthylguanosine qui les empêchent d'être incorporés dans l'orientation inverse pendant une synthèse in vitro de l'ARNm et constituent ainsi des = analogues de coiffe anti-inverse = (ARCA). La modification d'ARCA garantit que l'atome S est positionné précisément dans les sites actifs des protéines de liaison à la coiffe dans la machinerie de traduction et de décoiffage. Les nouveaux analogues S-ARCA sont résistants aux enzymes de décoiffage in vivo. Certains S-ARCA ont une affinité pour eIF4E plus élevée que les analogues correspondants ne contenant pas un groupe phosphorothioate. Lorsque des ARNm contenant divers S-ARCA sont introduits dans des cellules mises en culture, certains sont traduits jusqu'à cinq fois plus efficacement que les ARNm synthétisés avec l'analogue classique m7GpppG.