5-phenyluridine-5′-triphosphate | 1300529-53-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-phenyluridine-5′-triphosphate
• 英文别名: 5-phenyl-UTP；[[(2R,3S,4R,5R)-5-(2,4-dioxo-5-phenylpyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 1300529-53-6
• 化学式: C₁₅H₁₉N₂O₁₅P₃
• 分子量: 560.242
• InChiKey: FYOKSOSKGQVQPS-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  259
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-phenyluridine-5′-triphosphate 、 对氟苯甲醇 在 glucose-1-phosphate uridylyltransferase 作用下， 以 aq. buffer 为溶剂， 反应 2.0h， 生成 [[(2R,3S,4R,5R)-5-(2,4-dioxo-5-phenylpyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
  参考文献：
  名称：

  Enzymatic synthesis of nucleobase-modified UDP-sugars: scope and limitations

  摘要：

  Glucose-1-phosphate uridylyltransferase in conjunction with UDP-glucose pyrophosphorylase was found to catalyse the conversion of a range of 5-substituted UTP derivatives into the corresponding UDP-galactose derivatives in poor yield. Notably the 5-iodo derivative was not converted to UDP-sugar. In contrast, UDP-glucose pyrophosphorylase in conjunction with inorganic pyrophosphatase was particularly effective at converting 5-substituted UTP derivatives, including the iodo compound, into a range of gluco-configured 5-substituted UDP-sugar derivatives in good yields. Attempts to effect 400-epimerization of these 5-substituted UDP-glucose with UDP-glucose 4 ''-epimerase from yeast were unsuccessful, while use of the corresponding enzyme from Erwinia amylovora resulted in efficient epimerization of only 5-iodo-UDP-Glc, but not the corresponding 5-aryl derivatives, to give 5-iodo-UDP-Gal. Given the established potential for Pd-mediated cross-coupling of 5-iodo-UDP-sugars, this provides convenient access to the galacto-configured 5-substituted-UDP-sugars from gluco-configured substrates and 5-iodo-UTP. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2014.12.005
• 作为产物：
  描述：

  5-iodouridine-5′-monophosphate 在 四氮唑 、 potassium pyrophosphate 、 sodium tetrachloropalladate(II) 、 2,2'-二硫二吡啶 、 三正丁胺 、 trisodium tris(3-sulfophenyl)phosphine 、 caesium carbonate 、 三苯基膦 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 5-phenyluridine-5′-triphosphate
  参考文献：
  名称：

  探索 5-取代基对 5-芳基和 5-杂芳基尿嘧啶核苷酸的固有荧光的作用：一项系统研究†‡

  摘要：

  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

  DOI：

  10.1039/c3ob40485d

文献信息

• 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。
• 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.
• Enzymatic synthesis of nucleobase-modified UDP-sugars: scope and limitations
  作者：Ben A. Wagstaff、Martin Rejzek、Thomas Pesnot、Lauren M. Tedaldi、Lorenzo Caputi、Ellis C. O’Neill、Stefano Benini、Gerd K. Wagner、Robert A. Field

  DOI：10.1016/j.carres.2014.12.005

  日期：2015.3

  Glucose-1-phosphate uridylyltransferase in conjunction with UDP-glucose pyrophosphorylase was found to catalyse the conversion of a range of 5-substituted UTP derivatives into the corresponding UDP-galactose derivatives in poor yield. Notably the 5-iodo derivative was not converted to UDP-sugar. In contrast, UDP-glucose pyrophosphorylase in conjunction with inorganic pyrophosphatase was particularly effective at converting 5-substituted UTP derivatives, including the iodo compound, into a range of gluco-configured 5-substituted UDP-sugar derivatives in good yields. Attempts to effect 400-epimerization of these 5-substituted UDP-glucose with UDP-glucose 4 ''-epimerase from yeast were unsuccessful, while use of the corresponding enzyme from Erwinia amylovora resulted in efficient epimerization of only 5-iodo-UDP-Glc, but not the corresponding 5-aryl derivatives, to give 5-iodo-UDP-Gal. Given the established potential for Pd-mediated cross-coupling of 5-iodo-UDP-sugars, this provides convenient access to the galacto-configured 5-substituted-UDP-sugars from gluco-configured substrates and 5-iodo-UTP. (C) 2015 The Authors. Published by Elsevier Ltd.
• 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