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uridine 3'-O-phosphorothioate | 166533-20-6

中文名称
——
中文别名
——
英文名称
uridine 3'-O-phosphorothioate
英文别名
1-[(2R,3R,4S,5R)-4-dihydroxyphosphinothioyloxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
uridine 3'-O-phosphorothioate化学式
CAS
166533-20-6
化学式
C9H13N2O8PS
mdl
——
分子量
340.251
InChiKey
WDSMFARKTPJXQR-XVFCMESISA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 密度:
    1.79±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    -1.9
  • 重原子数:
    21
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.56
  • 拓扑面积:
    181
  • 氢给体数:
    5
  • 氢受体数:
    9

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Hydrolytic dethiophosphorylation and desulfurization of the monothioate analogues of uridine monophosphates under acidic conditions
    摘要:
    The hydrolytic reactions of uridine 2'-, 3'- and 5'-phosphoromonothioates (2'-, 3'- and 5'-UMPS) under acidic and neutral conditions have been followed by HPLC. Under slightly acidic conditions (pH 2-5), only pa-independent dethiophosphorylation to uridine takes place. This reaction is 200- to 300-fold as fast as dephosphorylation of the corresponding uridine monophosphates (UMP), presumably due to higher stability of the thiometaphosphate monoanion compared to metaphosphate anion. At pH > 5, i.e. at pH > pK(a2) of the thiophosphate moiety, the dethiophosphorylation is retarded with increasing basicity of the solution. At pH < 1, acid-catalysed desulfurization of 2'- and 3'-UMPS to an isomeric mixture of 2'/3'-UMP competes with their dethiophosphorylation. This reaction is suggested to proceed by a nucleophilic attack of the neighbouring hydroxy group on phosphorus. No such reaction occurs with 5'-UMPS. In contrast to 2'- and 3'-UMP, no sign of interconversion of 2'- and 3'-UMPS is detected.
    DOI:
    10.1039/p29960000771
  • 作为产物:
    描述:
    Thiophosphoric acid O-(4-cyano-phenyl) ester O'-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl] ester 在 Carbonate buffer 、 hydroxide羟基甲酸酯 作用下, 生成 uridine 3'-O-phosphorothioate1-[(2R,3R,4R,5R)-3-dihydroxyphosphinothioyloxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
    参考文献:
    名称:
    尿苷 3'-(芳基硫代磷酸酯)分子内醇解中的碱催化和离开基团依赖性
    摘要:
    还研究了尿苷 3'-(芳基硫代磷酸酯) (Up(S)Ar) 中碱催化的分子内酯交换反应对离去芳氧基 (pKa 7.1-10) 共轭酸酸度的依赖性关于催化剂的碱度 (pKa(BH) = 7-10.2)。所研究的硫代磷酸酯的合成是通过使用基于受保护的尿苷 3'-H-膦酸酯与适当的酚类缩合的方法来完成的。氢氧化物和咪唑催化的速率常数(25°C,0.25 M 离子强度)服从布朗斯台德线性自由能关系,获得的 β 离去基团 (βlg) 值分别为 -0.55 和 -0.63。4-硝基苯氧化物从相应的硫代磷酸酯中的一般碱催化释放也遵循与催化剂碱度有关的布朗斯台德关系 (β = 0.59)。
    DOI:
    10.1021/ja953399d
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文献信息

  • SERPINA1 IRNA COMPOSITIONS AND METHODS OF USE THEREOF
    申请人:Alnylam Pharmaceuticals, Inc.
    公开号:EP3412774A1
    公开(公告)日:2018-12-12
    The invention relates to RNAi agents, e.g., double-stranded RNAi agents, targeting the Serpina1 gene, and methods of using such RNAi agents to inhibit expression of Serpina1 and methods of treating subjects having a Serpina1 associated disease, such as a liver disorder.
    该发明涉及RNAi药剂,例如靶向Serpina1基因的双链RNAi药剂,以及使用这种RNAi药剂抑制Serpina1表达的方法,以及治疗患有Serpina1相关疾病(如肝脏疾病)的受试者的方法。
  • COMPOSITIONS AND METHODS FOR INHIBITING EXPRESSION OF THE LECT2 GENE
    申请人:ALNYLAM PHARMACEUTICALS, INC.
    公开号:US20180135057A1
    公开(公告)日:2018-05-17
    The invention relates to antisense polynucleotide agents targeting the LECT2 gene, and methods of using such antisense polynucleotide agents to inhibit expression of LECT2 and to treat subjects having a LECT2-associated disease, e.g., amyloidosis.
    这项发明涉及针对LECT2基因的反义多核苷酸药剂,以及利用这种反义多核苷酸药剂抑制LECT2表达并治疗患有LECT2相关疾病(例如淀粉样变性)的受试者的方法。
  • COMPLEMENT COMPONENT C5 iRNA COMPOSITIONS AND METHODS OF USE THEREOF
    申请人:Alnylam Pharmaceuticals, Inc.
    公开号:US20150247143A1
    公开(公告)日:2015-09-03
    The invention relates to iRNA, e.g., double-stranded ribonucleic acid (dsRNA), compositions targeting the complement component C5 gene, and methods of using such iRNA, e.g., dsRNA, compositions to inhibit expression of C5 and to treat subjects having a complement component C5-associated disease, e.g., paroxysmal nocturnal hemoglobinuria.
    该发明涉及iRNA,例如双链核糖核酸(dsRNA),针对补体成分C5基因的组合物,以及使用这种iRNA,例如dsRNA,组合物来抑制C5的表达并治疗患有补体成分C5相关疾病的受试者,例如周期性夜间血红蛋白尿。
  • TMPRSS6 IRNA COMPOSITIONS AND METHODS OF USE THEREOF
    申请人:Alnylam Pharmaceuticals, Inc.
    公开号:EP3828276A1
    公开(公告)日:2021-06-02
    The present invention relates to a double stranded RNAi agent capable of inhibiting expression of TMPRSS6 in a cell, wherein said double stranded RNAi agent comprises a sense strand and an antisense strand forming a double-stranded region, wherein said sense strand comprises at least 15 contiguous nucleotides differing by no more than 3 nucleotides from the nucleotide sequence of 5' - ACCUGCUUCUUCUGGUUCAUU - 3' (SEQ ID NO: 139), and said antisense strand comprises at least 15 contiguous nucleotides differing by no more than 3 nucleotides from the nucleotide sequence of 5'-AGAAUGAACCAGAAGAAGCAGGU-3' (SEQ ID NO: 187), wherein substantially all of the nucleotides of said sense strand and substantially all of the nucleotides of said antisense strand are modified nucleotides, and wherein said sense strand, said antisense strand or both strands is/are conjugated to a ligand attached at the 3'-terminus, 5'-terminus or both termini.
    本发明涉及一种能够抑制细胞中 TMPRSS6 表达的双链 RNAi 剂,其中所述双链 RNAi 剂包括形成双链区域的有义链和反义链,其中所述有义链包括至少 15 个连续的核苷酸,与 5' - ACCUGCUUCUUCUGUGUCAUU - 3' (SEQ ID NO. 139)的核苷酸序列相差不超过 3 个核苷酸,所述反义链包括至少 15 个连续的核苷酸,与 5'-AGAAUGAACCAGAUGUCAU - 3' (SEQ ID NO. 139)的核苷酸序列相差不超过 3 个核苷酸:139),所述反义链包括至少 15 个连续的核苷酸,与 5'-AGAAUGAACCAGAAGAAGCAGGU-3' (SEQ ID NO: 187)的核苷酸序列相差不超过 3 个核苷酸、 其中所述有义链的基本上所有核苷酸和所述反义链的基本上所有核苷酸都是修饰的核苷酸,并且所述有义链、所述反义链或两条链都与连接在 3'末端、5'末端或两条末端的配体共轭。
  • Serpina1 iRNA compositions and methods of use thereof
    申请人:Alnylam Pharmaceuticals, Inc.
    公开号:US10030244B2
    公开(公告)日:2018-07-24
    The invention relates to RNAi agents, e.g., double-stranded RNAi agents, targeting the Serpina1 gene, and methods of using such RNAi agents to inhibit expression of Serpina1 and methods of treating subjects having a Serpina1 associated disease, such as a liver disorder.
    本发明涉及针对Serpina1基因的RNAi制剂,如双链RNAi制剂,以及使用这种RNAi制剂抑制Serpina1表达的方法和治疗患有Serpina1相关疾病(如肝脏疾病)的受试者的方法。
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