5-(5-formylthien-2-yl)-uridine | 1300529-05-8

• 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: 5-(5-formylthien-2-yl)-uridine
• 英文别名: 5-(5-Formylthien-2-yl)-uridine；5-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]thiophene-2-carbaldehyde
• CAS: 1300529-05-8
• 化学式: C₁₄H₁₄N₂O₇S
• 分子量: 354.34
• InChiKey: UJELITGDRFBMQY-UORFTKCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-赖氨酸 、 5-(5-formylthien-2-yl)-uridine 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 25.0h， 以68%的产率得到2-((5-(1,2,3,4-tetrahydro-1-((2R,3R,4S,5R)-tetrahydro-3,4-dihydroxy-5-(hydroxymethyl)furan-2-yl)-2,4-dioxopyrimidin-5-yl)thiophen-2-yl)methylamino)-6-aminohexanoic acid
  参考文献：
  名称：

  Uncharged nucleoside inhibitors of β-1,4-galactosyltransferase with activity in cells

  摘要：

  5-取代尿苷衍生物是无电荷的半乳糖转移酶抑制剂，可以降低人单核细胞中PSGL-1的表达。

  DOI：

  10.1039/c5cc09289b
• 作为产物：
  描述：

  尿嘧啶核苷 在 sodium tetrachloropalladate(II) 水 、 碘 、 硝酸 、 caesium carbonate 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 5-(5-formylthien-2-yl)-uridine
  参考文献：
  名称：

  [EN] DERIVATIVES OF URIDINE PHOSPHATE AND THEIR USES IN PROTEIN BINDING ASSAYS
  [FR] COMPOSÉS ET LEURS UTILISATIONS DANS DES DOSAGES DE LIAISON AUX PROTÉINES

  摘要：

  公开号：

  WO2011051733A3

文献信息

• Exploring the role of the 5-substituent for the intrinsic fluorescence of 5-aryl and 5-heteroaryl uracil nucleotides: a systematic study
  作者：Thomas Pesnot、Lauren M. Tedaldi、Pablo G. Jambrina、Edina Rosta、Gerd K. Wagner

  DOI：10.1039/c3ob40485d

  日期：——

  and proticity. In conjunction with results from a conformational analysis based on NMR data and computational experiments, these findings provide insights into the steric and electronic factors that govern fluorescence emission in this class of fluorophores. In particular, they highlight the interplay between fluorescence emission and conformation in this series. Finally, we carried out ligand-binding

  UMP 的衍生物 (尿苷一磷酸) 在 5 位有一个荧光取代基，代表了一个小而独特的荧光团，在化学生物学和生物分子化学中发现了重要的应用。在这项研究中，我们合成了一系列在5位具有不同芳香族和杂芳香族取代基的尿嘧啶核苷酸UMP、UDP和UTP的衍生物，以系统地研究5-取代基对荧光发射的影响。我们已经确定了该系列中所有衍生物的相关光物理参数，包括最佳荧光团的量子产率。在尿嘧啶碱基的第 5 位使用 5-formylthien-2-yl 取代基观察到最强的荧光发射，而相应的 3-formylthien-2-yl-取代的区域异构体的荧光显着降低。在不同极性和质子的溶剂中进一步研究了 5-(5-formylthien-2-yl) 尿嘧啶荧光团。结合基于 NMR 数据和计算实验的构象分析结果，这些发现提供了对控制此类荧光团中荧光发射的空间和电子因素的见解。特别是，它们突出了本系列中荧光发射和构象之间的相互作用。最后，我们用
• DERIVATIVES OF URIDINE PHOSPHATE AND THEIR USES IN PROTEIN BINDING ASSAYS
  申请人：Wagner Gerd

  公开号：US20120219963A1

  公开（公告）日：2012-08-30

  The present invention relates to compounds and their use in competitive protein binding assays, for example for use with glycosyl transferase and/or glycoprocessing proteins. The present application also provides kits and apparatuses for use in the assays. In particular, the present invention provides a compound of the formula (I): wherein n is 1, 2 or 3; R 1 is selected from —OH, —OPO 3 H, —OR 4 , —NHR 4 , R 6 ; R 2 and R 3 are each independently selected from —H, —OH, optionally substituted —O-alkyl and —O-alkanoyl; R 4 is selected from an optionally substituted mono or polysaccharide, -alkyl, -alkenyl, -alkynyl, and L-Z, where L is a linking agent and Z is a binding agent; R 6 is an optionally substituted hydrocarbon group; A is either (i) a substituted heteroaryl group, the substituent on the heteroaryl group having a double bond conjugated to the heteroaryl group, or (ii) a substituted aryl group, the substituent on the aryl group having a double bond conjugated to the aryl group.

  本发明涉及化合物及其在竞争性蛋白结合测定中的应用，例如用于糖基转移酶和/或糖基加工蛋白的应用。本申请还提供用于该测定的试剂盒和装置。具体而言，本发明提供式（I）的化合物：其中n为1、2或3；R1选择自—OH、—OPO3H、—OR4、—NHR4、R6；R2和R3各自独立地选择自—H、—OH、可选地取代的—O-烷基和—O-酰基烷基；R4选择自可选地取代的单糖或多糖、-烷基、-烯基、-炔基和L-Z，其中L是连接剂，Z是结合剂；R6是可选地取代的烃基；A是（i）取代的杂环芳基，杂环芳基上的取代基具有共轭到杂环芳基的双键，或（ii）取代的芳基，芳基上的取代基具有共轭到芳基的双键。
• Derivatives of uridine phosphate and their uses in protein binding assays
  申请人：Wagner Gerd

  公开号：US09018370B2

  公开（公告）日：2015-04-28

  The present invention relates to compounds and their use in competitive protein binding assays, for example for use with glycosyl transferase and/or glycoprocessing proteins. The present application also provides kits and apparatuses for use in the assays. In particular, the present invention provides a compound of the formula (I): wherein n is 1, 2 or 3; R1 is selected from —OH, —OPO3H, —OR4, —NHR4, R6; R2 and R3 are each independently selected from —H, —OH, optionally substituted —O-alkyl and —O-alkanoyl; R4 is selected from an optionally substituted mono or polysaccharide, -alkyl, -alkenyl, -alkynyl, and L-Z, where L is a linking agent and Z is a binding agent; R6 is an optionally substituted hydrocarbon group; A is either (i) a substituted heteroaryl group, the substituent on the heteroaryl group having a double bond conjugated to the heteroaryl group, or (ii) a substituted aryl group, the substituent on the aryl group having a double bond conjugated to the aryl group.

  本发明涉及化合物及其在竞争性蛋白质结合测定中的应用，例如用于糖基转移酶和/或糖基加工蛋白质的应用。本申请还提供用于该测定的试剂盒和设备。具体而言，本发明提供了式（I）的化合物：其中n为1、2或3；R1选自—OH、—OPO3H、—OR4、—NHR4、R6；R2和R3各自独立地选自—H、—OH、可选地取代的—O-烷基和—O-酰基烷基；R4选自可选地取代的单糖或多糖、-烷基、-烯基、-炔基和L-Z，其中L是连接剂，Z是结合剂；R6是可选地取代的碳氢基团；A是（i）取代的杂芳基团，杂芳基团上的取代基具有与杂芳基团共轭的双键，或（ii）取代的芳基团，芳基团上的取代基具有与芳基团共轭的双键。
• US9018370B2
  申请人：——

  公开号：US9018370B2

  公开（公告）日：2015-04-28
• [EN] COMPOUNDS AND THEIR USES IN PROTEIN BINDING ASSAYS<br/>[FR] COMPOSÉS ET LEURS UTILISATIONS DANS DES DOSAGES DE LIAISON AUX PROTÉINES
  申请人：UNIV EAST ANGLIA

  公开号：WO2011051733A2

  公开（公告）日：2011-05-05

  The present invention relates to compounds and their use in competitive protein binding assays, for example for use with glycosyl transferase and/or glycoprocessing proteins. The present application also provides kits and apparatuses for use in the assays. In particular, the present invention provides a compound of the formula (I): wherein n is 1, 2 or 3; R1 is selected from -OH, -OPO3H, -OR4, -NHR4, R6; R2 and R3 are each independently selected from -H, -OH, optionally substituted -O- alkyl and -O-alkanoyl; R4 is selected from an optionally substituted mono or polysaccharide, -alkyl, -alkenyl, - alkynyl, and L-Z, where L is a linking agent and Z is a binding agent; R6 is an optionally substituted hydrocarbon group; A is either (i) a substituted heteroaryl group, the substituent on the heteroaryl group having a double bond conjugated to the heteroaryl group, or (ii) a substituted aryl group, the substituent on the aryl group having a double bond conjugated to the aryl group.