2',3'-O-bis[(tert-butyl)dimethylsilyl]-2-N-(4,4'-dimethoxytrityl)guanosine | 497070-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2',3'-O-bis[(tert-butyl)dimethylsilyl]-2-N-(4,4'-dimethoxytrityl)guanosine
• 英文别名: 2',3'-O-di-tert-butyldimethylsilyl-2-N-(4,4'-dimethoxytrityl)guanosine；9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(hydroxymethyl)oxolan-2-yl]-2-[[bis(4-methoxyphenyl)-phenylmethyl]amino]-3H-purin-6-one
• CAS: 497070-22-1
• 化学式: C₄₃H₅₉N₅O₇Si₂
• 分子量: 814.142
• InChiKey: OYKQTHVLAWVHBR-ZENBVRMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  57.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  141.98
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-bis[(tert-butyl)dimethylsilyl]-2-N-(4,4'-dimethoxytrityl)guanosine 在 四丁基氟化铵 、 1-甲基-5-巯基-1H-四氮唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.34h， 生成
  参考文献：
  名称：

  Structure–activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity

  摘要：

  To study the structure-activity relationship of phosmidosine, a variety of phosmidosine derivatives 9a-g were synthesized by condensation of N-diisopropyl N'-(N-tritylprolyl)phosphorodiamidite 6 with appropriately protected nucleoside derivatives 7a-g. As the result, replacement of the 7,8-diliydro-8-oxoadenine base by adenine and 6-N-acetyladenine did not affect the antitumor activity. However, phosmidosine derivatives containing uracil, cytosine, and guanine in place of the 7,8-dibydro-8-oxoadenine base did not show significant activity. A plausible explanation for the selective expression of phosmidosine compared with that of phosmidosine analogs having other amino acids in place of proline is also discussed. These results suggest that phosmidosine serves as an inhibitor of prolyl adenosine 5'-phosphate (prolyl-AMP) to inhibit the peptide synthesis in cancer-related cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.021
• 作为产物：
  描述：

  在 ammonium hydroxide 作用下， 以 吡啶 为溶剂， 反应 6.0h， 生成 2',3'-O-bis[(tert-butyl)dimethylsilyl]-2-N-(4,4'-dimethoxytrityl)guanosine
  参考文献：
  名称：

  Structure–activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity

  摘要：

  To study the structure-activity relationship of phosmidosine, a variety of phosmidosine derivatives 9a-g were synthesized by condensation of N-diisopropyl N'-(N-tritylprolyl)phosphorodiamidite 6 with appropriately protected nucleoside derivatives 7a-g. As the result, replacement of the 7,8-diliydro-8-oxoadenine base by adenine and 6-N-acetyladenine did not affect the antitumor activity. However, phosmidosine derivatives containing uracil, cytosine, and guanine in place of the 7,8-dibydro-8-oxoadenine base did not show significant activity. A plausible explanation for the selective expression of phosmidosine compared with that of phosmidosine analogs having other amino acids in place of proline is also discussed. These results suggest that phosmidosine serves as an inhibitor of prolyl adenosine 5'-phosphate (prolyl-AMP) to inhibit the peptide synthesis in cancer-related cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.021

文献信息

• ——
  作者：Masatoshi Ushioda、Michinori Kadokura、Tomohisa Moriguchi、Akio Kobori、Morihiro Aoyagi、Kohji Seio、Mitsuo Sekine

  DOI：10.1002/1522-2675(200209)85:9<2930::aid-hlca2930>3.0.co;2-2

  日期：2002.9

  In connection with the synthesis of guanosine-capped of oligodeoxynucleotides on polymer supports, we found an unprecedented Si-O bond cleavage reaction, which occurred when polymer-linked oligodeoxynucleoticles having unprotected internucleotidic phosphate groups were allowed to react with the guanosine 5'-phosphorimidazolide derivative 18 in the presence of 4-nitro-6-(trifluoromethyl)-1H-benzotriazol-1-ol (Ntbt-OH) as an effective activator in pyridine. This side reaction was confirmed by the fact that the liquid-phase reaction of DMTrTpT-O-Si(iPr(2))OEt 42 with a simpler model compound. methyl phosphorimidazolide 34. in the presence of Ntbt-OH gave DMTrTpT 43. It turned out that the side reaction hardly occurs without unprotected internucleotidic phosphate groups on oligodeoxyriucleotides. The detailed study of this side reaction disclosed that Ntbt-OH directly attacks the Si-atom to release oligonucleotides from the resin. It is likely that Ntbt-OH serves as a very strong nucleophile in pyridine, especially to the Si-atom of the linker.