tert-butyl 2-(6-amino-9H-purin-9-yl)acetate | 152774-16-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 2-(6-amino-9H-purin-9-yl)acetate
• 英文别名: 9-(tert-butyloxycarbonylmethyl)-adenine；tert-butyl (adenin-9-yl)acetate；tert-butyl 2-(6-aminopurin-9-yl)acetate
• CAS: 152774-16-8
• 化学式: C₁₁H₁₅N₅O₂
• 分子量: 249.272
• InChiKey: DLXYCJXQTOWEKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(6-amino-9H-purin-9-yl)acetate 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 9H-嘌呤-9-乙酸,6-(苯甲酰氨基)-
  参考文献：
  名称：

  Oligonucleotide Analogues with 4-Hydroxy-N-Acetylprolinol as Sugar Substitute

  摘要：

  AbstractModified oligonucleotides incorporating trans‐4‐hydroxy‐N‐acetyl‐L‐prolinol (trans‐4‐HO‐L‐NAP) or its D‐analogue as sugar substitute were synthesised with adenine and thymine as nucleobases. All‐adenine oligonucleotides built from (2S,4S) or (2R,4R)‐cis‐4‐hydroxy‐N‐acetylprolinol were likewise prepared. Hybridisation studies revealed that heterocomplexes formed between polyU and homochiral trans‐4‐hydroxy‐N‐acetylprolinol‐based oligomers of the same as well as of opposite chirality (polyU/trans‐DA*13 and polyU/trans‐LA*13). The former, however, were triple‐stranded. Other complexes with ribonucleic acids were polyA/trans‐LT*13 and polyU/cis‐LA*13. Heteroduplexes with deoxynucleic acids were formed between trans‐LA*13 and oligothymidylate. Interaction was also observed for cis‐LA*13 and oligothymidylate, but not with the D‐hydroxyprolinol analogues. Microcalorimetry proved this interaction to be the formation of a triple‐stranded complex. Two heteroduplexes, trans‐LA*13/dT13 and trans‐LA*13/polyU, had similar or slightly increased stability when compared to the natural dA13/dT13 or dA13/polyU systems. Microcalorimetry clearly indicated the formation of a duplex, in contrast to interactions with N‐acetylprolinol oligonucleotides of different stereochemistry. Moreover, the enthalpy change was of the same magnitude but the association constant was slightly lower. Natural nucleic acids thus clearly prefer hybridisation with L‐hydroxyprolinol oligomers over D‐hydroxyprolinol oligomers. For the series investigated, the L‐trans oligomers (Figure 1) seem best to mimic natural oligonucleotides. These modified oligonucleotides formed homocomplexes if both strands were of the same chirality, that is, homocomplexes formed between trans‐LA* and trans‐LT* and between trans‐DA* and trans‐DT*, reflecting the isochiral pu‐py pairing found in natural nucleic acids. Once more, however, calorimetry proved these to be triplex interactions. Heterochiral pairing was not observed between modified oligonucleotides, but only between modified oligonucleotides and natural polyU. The thermal stabilities of these heterochiral complexes differed clearly.

  DOI：

  10.1002/chem.19970031215
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 腺嘌呤 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 、 N,N-dimethyl-d₆-formamide 为溶剂， 以44 %的产率得到tert-butyl 2-(6-amino-9H-purin-9-yl)acetate
  参考文献：
  名称：

  一种与 Boc 化学兼容的安全保护基团策略，用于合成肽核酸 (PNA)

  摘要：

  肽核酸 (PNA) 是一类有趣的合成生物分子，在医学领域具有巨大潜力。尽管 PNA 可以被视为寡核苷酸的类似物，但它们的合成更像是肽的合成。在这两种情况下，都使用固相合成（SPS）方法。在此，使用Boc作为临时保护基团的优点已被证明比Fmoc更受青睐。在此背景下，基于侧链碱基和接头的环外氮的安全保护基团方案，开发了一种新的 PNA SPS 策略。含亚磺酰基（亚砜）的部分对于用于去除 Boc 基团的三氟乙酸 (TFA) 完全稳定，但它们可以还原为相应的硫化物衍生物，而这些衍生物在 TFA 存在下不稳定。这种新型合成策略的效率已在 PNA 五聚体 H–PNA(TATCT)–βAla–OH 的合成中得到证明。

  DOI：

  10.1039/d3ob01348k

文献信息

• Synthesis of nucleobase-caged peptide nucleic acids having improved photochemical properties
  作者：Takayoshi Watanabe、Tomoko Hoshida、Jun Sakyo、Mariko Kishi、Satoshi Tanabe、Junichi Matsuura、Shingo Akiyama、Makiko Nakata、Yasuaki Tanabe、Akinobu Z. Suzuki、Soichiro Watanabe、Toshiaki Furuta

  DOI：10.1039/c4ob00418c

  日期：——

  A nucleobase-caged peptide nucleic acid (PNA) having a (6-bromo-7-methoxycoumarin)-4-ylmethoxycarbonyl (Bmcmoc) caging group was newly synthesized.

  一个具有（6-溴-7-甲氧基香豆素）-4-甲氧羰基（Bmcmoc）保护基团的核碱基保护的肽核酸（PNA）被新合成。
• Ceulemans, G.; Aerschot, A. Van; Herdewijn, P., Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S234 - S237
  作者：Ceulemans, G.、Aerschot, A. Van、Herdewijn, P.

  DOI：——

  日期：——
• Synthesis of Potential Purinoceptor Antagonists: Application of P1-tBu Phosphazene Base for Alkylation of Adenine in Solution and on Solid Phase
  作者：Erki Enkvist、Gerda Raidaru、Asko Uri、Roshni Patel、Catherine Redick、José L. Boyer、Juhan Subbi、Indrek Tammiste

  DOI：10.1080/15257770500446857

  日期：2006.1

  Alkylation of adenine in solution and on solid phase was accelerated by phosphazene base P1-tBu compared to mineral bases. The reactions in solution afforded regioselectively the appropriate N9-alkylated adenines with high preparative yields while the reaction with polystyrene resin-bound N-bromoacetylated peptides gave three regioisomers (alkylated at the N9, N7, and N3 position of adenine) in a 4:2:1 molar ratio. Ten novel nonphosphate nucleotide analogues were tested in an ADP-induced platelet aggregation assay.
• Solid-Phase Synthesis of 4(5),1′,5′-Trisubstituted 2,4′-Biimidazoles
  作者：Tuomas Karskela、Harri Lönnberg

  DOI：10.1021/jo902122e

  日期：2009.12.18

  A method for the synthesis of libraries of 4(5), 1',5'-tri substituted 2,4'-biimidazoles on a solid support was developed.(1) A trivalent scaffold, 2-(5'-amino-4(5)-formyl-1H,1'H-2,4'-biimidazol-1'-yl)acetic acid, was first prepared in solution by a two-step synthesis from ethyl adenin-9-ylacetate and bromomalonaldehyde. The product was coupled to an amino acid loaded Wang resin and the formyl group was subsequently derivatized either by reductive amination, oximation, or hydrazone formation. The 5'-amino group of the resin-bound biimidazole was then acylated and the products were finally released from the resin and purified. 5'-Amino-2,4'-biimidazole offers a scaffold for lead compounds of drug discovery, possibly useful in finding leads for protein kinase inhibitors.
• Rasmussen, Malcolm; Hope, Janet M., Australian Journal of Chemistry, 1982, vol. 35, # 3, p. 535 - 542
  作者：Rasmussen, Malcolm、Hope, Janet M.

  DOI：——

  日期：——