8-(4-chlorophenylthio)adenosine-5’-O-monophosphate | 78710-84-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 8-(4-chlorophenylthio)adenosine-5’-O-monophosphate
• 英文别名: 8-pCPT-5’-AMP；8-(4-Chlorophenylthio)adenosine-5'-monophosphate；[(2R,3S,4R,5R)-5-[6-amino-8-(4-chlorophenyl)sulfanylpurin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 78710-84-6
• 化学式: C₁₆H₁₇ClN₅O₇PS
• 分子量: 489.833
• InChiKey: FAGBMJWRFRHMCM-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  211
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  8-(4-chlorophenylthio)adenosine-5’-O-monophosphate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 [[(2R,3S,4R,5R)-5-[6-amino-8-(4-chlorophenyl)sulfanylpurin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl hydrogen phosphate
  参考文献：
  名称：

  SAR Analysis of Adenosine Diphosphate (Hydroxymethyl)pyrrolidinediol Inhibition of Poly(ADP-ribose) Glycohydrolase

  摘要：

  Polyadenosine diphosphoribose glycohydrolase (PARG) catalyzes the intracellular hydrolysis of adenosine diphosphoribose polymers. Because structure-activity data are lacking for PARG, the specific inhibitor adenosine diphosphate (hydroxymethyl)pyrrolidinediol (ADP-HPD) was utilized to determine the effects of structure on inhibitor potency using PARG isolated from bovine thymus (bPARG) and recombinant bovine PARG catalytic fragment (rPARG-CF). Both enzymes were strongly inhibited by submicromolar levels of ADP-HPD, but ADP and the phosphorylated pyrrolidine displayed no activity. Utilizing ADP-HPD analogues containing 2-, N-6, or 8-adenosyl substituents or guanine instead of adenine, the importance of adenine ring recognition as well as a correlation between loss of PARG inhibition and the length and bulkiness of 8-adenosyl substituents was shown. Utilization of ADP-HPD analogues lacking one or both pyrrolidine cis-hydroxyls demonstrated their importance for inhibitor binding. Last, the similarity between naturally occurring bPARG and heterologously expressed rPARG-CF was demonstrated. Therefore, readily available rPARG-CF is suitable for use in future studies to determine the structural aspects of PARG.

  DOI：

  10.1021/jm020541u
• 作为产物：
  描述：

  8-bromoadenosine-5'-monophosphate 、 4-氯苯硫酚 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以4%的产率得到8-(4-chlorophenylthio)adenosine-5’-O-monophosphate
  参考文献：
  名称：

  Inhibition of inosinic acid dehydrogenase by 8-substituted purine nucleotides

  摘要：

  A series of 8-substituted derivatives of adenosine monophosphate (AMP) and inosine monophosphate (IMP) were synthesized and examined for their ability to inhibit Escherichia coli IMP dehydrogenase. All compounds studied were competitive inhibitors in IMP-dependent competition studies and lacked substrate activity. In oxidized nicotinamide adenine dinucleotide dependent studies, 8-(p-NO2PhCH2S)-IMP was noncompetitive and 8-(p-NO2PhCH2S)-AMP showed mixed inhibition. Multiple regression analysis showed that for the series of 8-(para-substituted-benzylthio)-AMPs and -IMPs, the electron-withdrawing ability of the para substituent on the benzylthio moiety correlated best with log Ki of the analogues.

  DOI：

  10.1021/jm00142a007

文献信息

• Methods for modulating taste receptors
  申请人：MARS, INCORPORATED

  公开号：US11185100B2

  公开（公告）日：2021-11-30

  Amino acids present in domains of an umami taste receptor are described herein, wherein the amino acids interact with at least one nucleotide derivative and/or at least one transmembrane compound that potentiates, modulates, increases, and/or enhances the activity of the umami receptor. Such compounds can be used in flavor compositions to enhance the umami taste and/or palatability of food products.

  本文描述了存在于鲜味受体结构域中的氨基酸，其中氨基酸与至少一种核苷酸衍生物和/或至少一种跨膜化合物相互作用，从而增强、调节、增加和/或提高鲜味受体的活性。此类化合物可用于调味组合物，以增强食品的鲜味和/或适口性。
• FLAVOR COMPOSITIONS AND PET FOOD PRODUCTS CONTAINING THE SAME
  申请人：Mars, Incorporated

  公开号：EP3229610B1

  公开（公告）日：2021-06-09
• METHODS FOR MODULATING TASTE RECEPTORS
  申请人：MARS, INCORPORATED

  公开号：US20180255813A1

  公开（公告）日：2018-09-13

  Amino acids present in domains of an umami taste receptor are described herein, wherein the amino acids interact with at least one nucleotide derivative and/or at least one transmembrane compound that potentiates, modulates, increases, and/or enhances the activity of the umami receptor. Such compounds can be used in flavor compositions to enhance the umami taste and/or palatability of food products.
• SAR Analysis of Adenosine Diphosphate (Hydroxymethyl)pyrrolidinediol Inhibition of Poly(ADP-ribose) Glycohydrolase
  作者：David W. Koh、Donna L. Coyle、Nimish Mehta、Sushma Ramsinghani、Hyuntae Kim、James T. Slama、Myron K. Jacobson

  DOI：10.1021/jm020541u

  日期：2003.9.1

  Polyadenosine diphosphoribose glycohydrolase (PARG) catalyzes the intracellular hydrolysis of adenosine diphosphoribose polymers. Because structure-activity data are lacking for PARG, the specific inhibitor adenosine diphosphate (hydroxymethyl)pyrrolidinediol (ADP-HPD) was utilized to determine the effects of structure on inhibitor potency using PARG isolated from bovine thymus (bPARG) and recombinant bovine PARG catalytic fragment (rPARG-CF). Both enzymes were strongly inhibited by submicromolar levels of ADP-HPD, but ADP and the phosphorylated pyrrolidine displayed no activity. Utilizing ADP-HPD analogues containing 2-, N-6, or 8-adenosyl substituents or guanine instead of adenine, the importance of adenine ring recognition as well as a correlation between loss of PARG inhibition and the length and bulkiness of 8-adenosyl substituents was shown. Utilization of ADP-HPD analogues lacking one or both pyrrolidine cis-hydroxyls demonstrated their importance for inhibitor binding. Last, the similarity between naturally occurring bPARG and heterologously expressed rPARG-CF was demonstrated. Therefore, readily available rPARG-CF is suitable for use in future studies to determine the structural aspects of PARG.
• Inhibition of inosinic acid dehydrogenase by 8-substituted purine nucleotides
  作者：Edward B. Skibo、Rich B. Meyer

  DOI：10.1021/jm00142a007

  日期：1981.10

  A series of 8-substituted derivatives of adenosine monophosphate (AMP) and inosine monophosphate (IMP) were synthesized and examined for their ability to inhibit Escherichia coli IMP dehydrogenase. All compounds studied were competitive inhibitors in IMP-dependent competition studies and lacked substrate activity. In oxidized nicotinamide adenine dinucleotide dependent studies, 8-(p-NO2PhCH2S)-IMP was noncompetitive and 8-(p-NO2PhCH2S)-AMP showed mixed inhibition. Multiple regression analysis showed that for the series of 8-(para-substituted-benzylthio)-AMPs and -IMPs, the electron-withdrawing ability of the para substituent on the benzylthio moiety correlated best with log Ki of the analogues.