9-(β-D-xylofuranosyl)-adenine-5'-monophosphate | 29740-88-3

• 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: 9-(β-D-xylofuranosyl)-adenine-5'-monophosphate
• 英文别名: 9-β-D-Xylofuranosyl-adenin-5'-phosphat；ara-Adenosin-5'-phosphat；9-(5-O-phosphono-beta-D-xylofuranosyl)-9H-purin-6-amine；[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 29740-88-3
• 化学式: C₁₀H₁₄N₅O₇P
• 分子量: 347.224
• InChiKey: UDMBCSSLTHHNCD-GAWUUDPSSA-N

物化性质

• 熔点：
  208 °C (decomp)
• 沸点：
  798.5±70.0 °C(Predicted)
• 密度：
  2.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  9-(β-D-xylofuranosyl)-adenine-5'-monophosphate 、 2',3'-di-O-acetylnicotinamide mononucleotide 在 三正丁胺 、 氯磷酸二苯酯 、 吡啶 、 三辛胺 、 氨 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 43.0h， 生成
  参考文献：
  名称：

  Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose

  摘要：

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.012
• 作为产物：
  描述：

  N⁶-benzoyl-9-(2,3-di-O-benzoyl-β-D-xylofuranosyl)adenine 在 磷酸三乙酯 、 氨 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 37.0h， 生成 9-(β-D-xylofuranosyl)-adenine-5'-monophosphate
  参考文献：
  名称：

  Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose

  摘要：

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.012

文献信息

• TSLP promotes immune evasion and persistence of viruses
  申请人：Institut Curie

  公开号：EP2213682A1

  公开（公告）日：2010-08-04

  The invention relates to the treatment or prevention of a chronic viral infection with a Thymic Stromal Lymphopoietin (TSLP) antagonist thereby avoiding immune evasion and persistence of the virus. The invention also provides a method of prognosing the evolution of a cervical dysplasia by TSLP expression in a sample of said cervical dysplasia.

  本发明涉及用胸腺间质淋巴细胞生成素（TSLP）拮抗剂治疗或预防慢性病毒感染，从而避免免疫逃避和病毒持续存在。本发明还提供了一种通过宫颈发育不良样本中 TSLP 的表达预测宫颈发育不良演变的方法。
• TSLP PROMOTES IMMUNE EVASION AND PERSISTENCE OF VIRUSES
  申请人：Institut Curie

  公开号：EP2391649A1

  公开（公告）日：2011-12-07
• Pathway Analysis of Cell Culture Phenotypes and Uses Thereof
  申请人：Melville Mark

  公开号：US20090186358A1

  公开（公告）日：2009-07-23

  The present invention provides methods for systematically identifying genes, proteins and/or related pathways that regulate or indicative of cell phenotypes. The present invention further provides methods for manipulating the identified genes, proteins and/or pathways to engineer improved cell lines and/or to evaluate or select cell lines with desirable phenotypes.
• [EN] TSLP PROMOTES IMMUNE EVASION AND PERSISTENCE OF VIRUSES<br/>[FR] LA TSLP FAVORISE L'ÉVASION IMMUNITAIRE ET LA PERSISTANCE DE VIRUS
  申请人：INST CURIE

  公开号：WO2010086445A1

  公开（公告）日：2010-08-05

  The invention relates to the treatment or prevention of a chronic viral infection with a Thymic Stromal Lymphopoietin (TSLP) antagonist thereby avoiding immune evasion and persistence of the virus. The invention also provides a method of prognosing the evolution of a cervical dysplasia by TSLP expression in a sample of said cervical dysplasia.
• Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose
  作者：Christopher J.W Mort、Marie E Migaud、Antony Galione、Barry V.L Potter

  DOI：10.1016/j.bmc.2003.10.012

  日期：2004.1

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.