5'-O-[(L-prolyl)-sulfamoyl]adenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 5'-O-[(L-prolyl)-sulfamoyl]adenosine
• 英文别名: (2Z,2S)-N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxysulfonyl]pyrrolidin-1-ium-2-carboximidate
• 化学式: C₁₅H₂₁N₇O₇S
• 分子量: 443.44
• InChiKey: LKVJEMXWEODCAY-JVEUSOJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  212
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 氨基磺酰氯 、 sodium hydride 、 三氟乙酸 、 1,8-diazabicyclo-[5,4,0]-undecane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 5'-O-[(L-prolyl)-sulfamoyl]adenosine
  参考文献：
  名称：

  Synthesis and Aminoacyl-tRNA Synthetase Inhibitory Activity of Prolyl Adenylate Analogs

  摘要：

  Two nonhydrolyzable prolyl adenylate analogs, 5'-O-[N-(L-prolyl)-sulfamoyl]adenosine (L-PSA) and 5'-O-[N-(D-prolyl)-sulfamoyl] adenosine (D-PSA), were prepared in three steps from 2',3'-di-O-isopropylideneadenosine. Both of these compounds inhibited the in vitro activity of Escherichia coli and human prolyl-tRNA synthetase (ProRS). The human enzyme used in this study was derived from the carboxy-terminal domain of the multifunctional human EPRS gene. The K-i(ATP) values for L-PSA, determined using the ATP-PPi exchange assay, are very similar for both synthetases (approximate to 1-2 nM). The K-i(Pro) values, on the other hand, vary approximately seven-fold between the two synthetases (0.6 nM for human and 4.3 nM for E. coli). The K-i values measured for the D-PSA analog are much higher (51-470 nM) for all cases examined; however, the same species-specific differences are observed with respect to K-i(Pro). These results indicate possible structural differences in or near the active sites of the two enzymes that may be exploited in the future design of compounds that function as species-specific synthetase inhibitors in vivo. (C) 1996 Academic Press, Inc.

  DOI：

  10.1006/bioo.1996.0025

文献信息

• Advanced drug development and manufacturing
  申请人：ICAGEN, LLC

  公开号：US10877035B2

  公开（公告）日：2020-12-29

  X-ray fluorescence (XRF) spectrometry has been used for detecting binding events and measuring binding selectivities between chemicals and receptors. XRF may also be used for estimating the therapeutic index of a chemical. For estimating the binding selectivities of a chemical versus chemical analogs, for measuring post translational modification of proteins, and for drug manufacturing.

  X 射线荧光 (XRF) 光谱法已被用于检测化学物质与受体之间的结合事件和测量结合选择性。XRF 还可用于估算化学品的治疗指数。XRF 还可用于估算化学品的治疗指数、估算化学品与化学类似物的结合选择性、测量蛋白质的翻译后修饰以及药物生产。
• ADVANCED DRUG DEVELOPMENT AND MANUFACTURING
  申请人：Los Alamos National Security, LLC

  公开号：EP2084519A2

  公开（公告）日：2009-08-05
• X-ray microscope
  申请人：XRpro Sciences, Inc.

  公开号：EP2511844B1

  公开（公告）日：2015-08-12
• INHIBITION OF TRNA SYNTHETASES AND THERAPEUTIC APPLICATIONS THEREOF
  申请人：Whitman Malcolm

  公开号：US20120058133A1

  公开（公告）日：2012-03-08

  The present invention provides novel methods for modulating Th 17-mediated immune responses using aminoacyl tRNA synthetase inhibitors. Inhibition of aminoacyl tRNA synthetase inhibitors activates an amino acid starvation response (AAR) and can produce beneficial therapeutic effects. In some embodiments, aminoacyl tRNA synthetase inhibitors are used to treat disorders such as autoimmune diseases, graft rejection, infections, fibrosis, and inflammatory diseases.
• Advanced Drug Development and Manufacturing
  申请人：XRpro Sciences, Inc.

  公开号：US20150309021A1

  公开（公告）日：2015-10-29

  X-ray fluorescence (XRF) spectrometry has been used for detecting binding events and measuring binding selectivities between chemicals and receptors. XRF may also be used for estimating the therapeutic index of a chemical. For estimating the binding selectivities of a chemical versus chemical analogs, for measuring post translational modification of proteins, and for drug manufacturing.