N⁶-benzoyl-β-L-adenosine | 868663-26-7

• 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: N⁶-benzoyl-β-L-adenosine
• 英文别名: L-N⁶-benzoyladenosine；N-Benzoyladenosine；N-[9-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 868663-26-7
• 化学式: C₁₇H₁₇N₅O₅
• 分子量: 371.352
• InChiKey: NZDWTKFDAUOODA-PYERRIOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-β-L-adenosine 在 吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-tetrahydrofuran-2-yl-N6-benzoyl-L-adenosine
  参考文献：
  名称：

  Synthesis and structural characterization of diastereomeric isomers of RNA trimer adenylyl(3′-5′)adenylyl(3′-5′)adenosine

  摘要：

  We have synthesized the diastereomeric isomers of adenylyl(3'-5')adenylyl(3'-5')adenosine (ApApA), and investigated their helical structures and hybridization properties with D-poly(U) by circular dichroism (CD) and UV melting experiments. The configuration of the 5'-end residue of ApApA has little effect on the helical structure. The configuration of the 3'-end residue has little effect on the stability of the triplex, and the chiral modifications cause complicated effects on the helical structure of ApApA and its triplex-forming ability with D-poly(U), depending on the site of the modification. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.026
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-β-L-呋喃核糖 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 吡啶 为溶剂， 反应 4.75h， 生成 N⁶-benzoyl-β-L-adenosine
  参考文献：
  名称：

  Visser, G. M.; van Westrenen, J.; van Boeckel, C. A. A., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 528 - 537

  摘要：

  DOI：

文献信息

• Enzymatic Parallel Kinetic Resolution of Mixtures of <scp>d</scp>/<scp>l</scp> 2′-Deoxy and Ribonucleosides: An Approach for the Isolation of β-<scp>l</scp>-Nucleosides
  作者：Saúl Martínez-Montero、Susana Fernández、Yogesh S. Sanghvi、Vicente Gotor、Miguel Ferrero

  DOI：10.1021/jo101368z

  日期：2010.10.1

  We have developed a lipase-catalyzed parallel kinetic resolution of mixtures of beta-D/L-nucleosides. The opposite selectivity during acylation exhibited by Pseudomonas cepacia lipase (PSL-C) with beta-D- and beta-L-nucleosides furnished acylated compounds that have different R-f values. As a consequence, isolation of both products was achieved by simple column chromatography. Computer modeling of the transition-state analogues during acylation of beta-D- and beta-L-2'-deoxycytidine with PSL-C was carried out to explain the high selectivity. PSL-C favored the 3'-O-levulination of the beta-D enantiomer, whereas the 5'-OH group was acylated in 2'-deoxy-beta-L-cytidine. In both cases, the cytosine base was placed in the alternate hydrophobic pocket of PSL's substrate-binding site, where it can form extra hydrogen bonds (in addition to the five essential catalytically relevant hydrogen bonds) that stabilize these intermediates catalyzing the selective acylation of beta-D/L-nucleosides.
• Synthesis and biological activities of 5′-ethylenic and acetylenic modified l-nucleosides and isonucleosides
  作者：Jun-Feng Wang、Xiao-Da Yang、Liang-Ren Zhang、Zhen-Jun Yang、Li-He Zhang

  DOI：10.1016/j.tet.2004.06.131

  日期：2004.9

  Two series of 6'-halovinyl-adenosine stereoisomers including 5'-ethylenic and acetylenic substituted L-adenosine, 5'-ethylenic and acetylenic substituted isonucleosides were synthesized. In the L-nucleoside series, compounds 6b, 8b, 10b and 13b showed modest inhibition of SAH hydrolase (21, 44, 50 and 26% respectively) at 100 muM. The L-isomers of 5'-ethylenic and acetylenic modified isonucleoside 23, 24 exhibited no activity for the inhibition of SAH hydrolase, however, the D-isomers 30 and 31 showed some activities in the same test (35 and 21%). It indicated clearly the strict stereochemical requirement for the substrate of SAH hydrolase. Compounds 6b, 8b, 8c, 11b exhibited modest to good inhibition effects on the growth of HeLa cells or Bel-7420 cells at 1 muM (64, 44, 53 and 82% respectively). (C) 2004 Elsevier Ltd. All rights reserved.
• Visser, G. M.; van Westrenen, J.; van Boeckel, C. A. A., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 528 - 537
  作者：Visser, G. M.、van Westrenen, J.、van Boeckel, C. A. A.、van Boom, J. H.

  DOI：——

  日期：——
• Synthesis and structural characterization of diastereomeric isomers of RNA trimer adenylyl(3′-5′)adenylyl(3′-5′)adenosine
  作者：Hidehito Urata、Hisafumi Hara、Yoshihiro Hirata、Norihiko Ohmoto、Masao Akagi

  DOI：10.1016/j.tetasy.2005.07.026

  日期：2005.9

  We have synthesized the diastereomeric isomers of adenylyl(3'-5')adenylyl(3'-5')adenosine (ApApA), and investigated their helical structures and hybridization properties with D-poly(U) by circular dichroism (CD) and UV melting experiments. The configuration of the 5'-end residue of ApApA has little effect on the helical structure. The configuration of the 3'-end residue has little effect on the stability of the triplex, and the chiral modifications cause complicated effects on the helical structure of ApApA and its triplex-forming ability with D-poly(U), depending on the site of the modification. (c) 2005 Elsevier Ltd. All rights reserved.