3'-deoxy-3'-fluoro-adenosine 5'-monophosphate | 121850-85-9

• 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: 3'-deoxy-3'-fluoro-adenosine 5'-monophosphate
• 英文别名: 3'-deoxy-3'-fluoroadenosine 5'-monophosphate；[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-3-fluoro-4-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 121850-85-9
• 化学式: C₁₀H₁₃FN₅O₆P
• 分子量: 349.215
• InChiKey: YARNDPZCUIYKLZ-QYYRPYCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 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：
  166
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-fluoro-adenosine 5'-monophosphate 在 三正丁胺 、 Aplysia cyclase 、 HEPES buffer 、 氯磷酸二苯酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 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-苯甲酰基腺嘌呤 在 吡啶 、 磷酸三乙酯 、 氨 、 六甲基二硅氮烷 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 108.0h， 生成 3'-deoxy-3'-fluoro-adenosine 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

• Potent Inhibitors of Human Inosine Monophosphate Dehydrogenase Type II. Fluorine-Substituted Analogs of Thiazole-4-carboxamide Adenine Dinucleotide
  作者：Andrzej Zatorski、Barry M. Goldstein、Thomas D. Colby、Jeffery P. Jones、Krzysztof W. Pankiewicz

  DOI：10.1021/jm00007a007

  日期：1995.3

  best cofactor-type inhibitor, beta-CH2-TAD (Ki = 0.11 microM). Interestingly, the level of inhibition of horse liver alcohol dehydrogenase by these compounds was found to be much lower (0.1 mM for 1 and 2 and no inhibition up to 10 mM for 3). These findings show that inhibition of tumor-induced inosine monophosphate dehydrogenase type II is selective and may be of therapeutic interest.

  噻唑-4-羧酰胺腺嘌呤二核苷酸（TAD）（1-3）的三个类似物分别在腺嘌呤核苷的C2'（核糖和阿拉伯糖构型）和C3'（核糖构型）中含有氟原子。由2'-脱氧-2'-氟腺苷（9），9-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）-腺嘌呤（17）和3的相应5'-单磷酸盐高收率合成'-deoxy-3'-氟腺苷（14）。通过将被保护的噻唑呋喃磷酸化，然后用羰基二咪唑处理并进行HPLC纯化，获得纯的2'，3'-O-异亚丙基-噻唑呋喃5'-磷酸咪唑啉（8）。8在DMF-d7中（由1H和31P NMR监测）中的9与9的反应得到所需的二核苷酸12，在脱异丙基化之后，其收率为82％，为1。在主要产品12的HPLC纯化过程中，还分离出少量对称的二核苷酸AppA（10，7.2％）和TRppTR（11，8.0％）。以类似的方式，通过将8与14和C偶联，得到化合物2和3。分别以80％和76％的收率排名第17位。我们早
• MIXAJLOPULO, I. A.;PRIKOTA, T. I.;PUPEJKO, N. E.;SIVETS, G. G.;KVASYUK, E+, 9 SOV.-IND. SIMP. PO XIMII PRIROD. SOED., RIGA, 15-18 MAYA, 1989, RIGA,(1+
  作者：MIXAJLOPULO, I. A.、PRIKOTA, T. I.、PUPEJKO, N. E.、SIVETS, G. G.、KVASYUK, E+

  DOI：——

  日期：——
• JP1022895A
  申请人：——

  公开号：JP1022895A

  公开（公告）日：1989-01-25
• US5658890A
  申请人：——

  公开号：US5658890A

  公开（公告）日：1997-08-19
• 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.