(Z)-4-(5'-deoxyadenosin-5'-ylidene)butanoic acid | 1040754-35-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (Z)-4-(5'-deoxyadenosin-5'-ylidene)butanoic acid
• 英文别名: (Z)-5-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]pent-4-enoic acid
• CAS: 1040754-35-5
• 化学式: C₁₄H₁₇N₅O₅
• 分子量: 335.319
• InChiKey: ZZPNPWVYLOIHPM-RSPDOVAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl (Z)-4-(5'-deoxyadenosin-5'-ylidene)butanoate 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到(Z)-4-(5'-deoxyadenosin-5'-ylidene)butanoic acid
  参考文献：
  名称：

  Synthesis of 5′-functionalized nucleosides: S-Adenosylhomocysteine analogues with the carbon-5′ and sulfur atoms replaced by a vinyl or halovinyl unit

  摘要：

  Adenosine and uridine analogues functionalized with alkenyl or. uoroalkenyl chain at C5' were prepared employing cross-metathesis, Negishi couplings, and Wittig reactions. Metathesis of the protected 5'-deoxy-5'- methyleneadenosine or uridine analogues with six-carbon amino acids (homoallylglycines) in the presence of Grubbs catalysts gave nucleoside analogues with the C5'-C6' double bond. Alternatively, the Pd-catalyzed cross-coupling between the protected 5'-deoxy-5'-(iodomethylene) nucleosides and suitable alkylzinc bromides also provided analogues with alkenyl unit. Stereoselective Pd-catalyzed monoalkylation of 5'-(bromofluoromethylene)-5'-deoxyadenosine with alkylzinc bromides afforded adenosylhomocysteine analogues with a 6'-(fluoro) vinyl motif. The vinylic adenine nucleosides produced time-dependent inactivation of the S-adenosyl-L-homocysteine hydrolases. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.017

文献信息

• Synthesis of 5′-functionalized nucleosides: S-Adenosylhomocysteine analogues with the carbon-5′ and sulfur atoms replaced by a vinyl or halovinyl unit
  作者：Stanislaw F. Wnuk、Pablo R. Sacasa、Elzbieta Lewandowska、Daniela Andrei、Sumin Cai、Ronald T. Borchardt

  DOI：10.1016/j.bmc.2008.04.017

  日期：2008.5

  Adenosine and uridine analogues functionalized with alkenyl or. uoroalkenyl chain at C5' were prepared employing cross-metathesis, Negishi couplings, and Wittig reactions. Metathesis of the protected 5'-deoxy-5'- methyleneadenosine or uridine analogues with six-carbon amino acids (homoallylglycines) in the presence of Grubbs catalysts gave nucleoside analogues with the C5'-C6' double bond. Alternatively, the Pd-catalyzed cross-coupling between the protected 5'-deoxy-5'-(iodomethylene) nucleosides and suitable alkylzinc bromides also provided analogues with alkenyl unit. Stereoselective Pd-catalyzed monoalkylation of 5'-(bromofluoromethylene)-5'-deoxyadenosine with alkylzinc bromides afforded adenosylhomocysteine analogues with a 6'-(fluoro) vinyl motif. The vinylic adenine nucleosides produced time-dependent inactivation of the S-adenosyl-L-homocysteine hydrolases. (C) 2008 Elsevier Ltd. All rights reserved.