2-(2-amino-6-(benzyloxy)-9H-purin-9-yl)acetic acid | 149411-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-(2-amino-6-(benzyloxy)-9H-purin-9-yl)acetic acid
• 英文别名: 2-amino-6-benzyloxy-9-carboxymethylpurine；(2-amino-6-(benzyloxy)purine-9-yl)acetic acid；(2-amino-6-(benzyloxy)purin-9-yl)acetic acid；[2-amino-6-(benzyloxy)purin-9-yl]acetic acid；2-amino-6-benzyloxy-N-9-carboxymethylpurine；(2-amino-6-benzyloxypurin-9-yl)acetic acid；2-(2-amino-6-phenylmethoxypurin-9-yl)acetic acid
• CAS: 149411-94-9
• 化学式: C₁₄H₁₃N₅O₃
• 分子量: 299.289
• InChiKey: IZJISFYAFBRVRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  159-165 °C(Solv: ethanol (64-17-5))
• 沸点：
  648.1±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-amino-6-(benzyloxy)-9H-purin-9-yl)acetic acid 在 溴 作用下， 以 乙酸乙酯 为溶剂， 反应 1.67h， 以61%的产率得到[O6-benzyl-8-bromo-guanin-9-yl]acetic acid
  参考文献：
  名称：

  8-Vinylguanine Nucleo Amino Acid: A Fluorescent PNA Building Block

  摘要：

  Attachment of a vinyl group at guanine position 8 provides fluorescent properties of the nucleobase. Therefore, 8-vinylguanine was introduced as a 2-aminoethylglycine peptide nucleic acid (PNA) building block. Incorporation of the guanine analog in short PNA sequences by Fmoc solid phase peptide synthesis allowed the differentiation between hybridization states of specific double strands with DNA, RNA, and PNA as well as quadruplex forming RNA/PNA oligomers based on fluorescence intensity.

  DOI：

  10.1021/ol3000603
• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 三乙烯二胺 、 lithium hydroxide 、 sodium hydride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 2-(2-amino-6-(benzyloxy)-9H-purin-9-yl)acetic acid
  参考文献：
  名称：

  基于环状PNA六聚体的化合物：HIV-1 RNA二聚化过程的建模，合成和抑制

  摘要：

  由（i）与HIV-1二聚化起始位点环的九个残基中的六个残基互补的六聚PNA部分和（ii）将PNA的N端与C端束缚在一起的间隔物构成的环状分子已经成为详细阐述了抑制HIV-1基因组的二聚化过程。该化合物是按照液相程序（完全保护的骨架方法）合成的。初步琼脂糖凝胶电泳分析表明，环状PNA偶联物能够抑制HIV-1二聚化。

  DOI：

  10.1016/s0040-4020(02)00527-6

文献信息

• A Peptide Nucleic Acid Embedding a Pseudopeptide Nuclear Localization Sequence in the Backbone Behaves as a Peptide Mimic
  作者：Stefano Sforza、Tullia Tedeschi、Alessandro Calabretta、Roberto Corradini、Consuelo Camerin、Roberto Tonelli、Andrea Pession、Rosangela Marchelli

  DOI：10.1002/ejoc.201000123

  日期：2010.5

  paper, the synthesis of a short modified peptide nucleic acid (PNA), obtained by using several different L-amino acids as synthons, is shown. The synthesis was performed by a submonomeric strategy, obtaining a model trimeric PNA containing embedded amino acid derived side chains in its backbone that mimic the peptide sequence PKKKRKV, which is a nuclear localization signal (NLS) widely used for translocating

  在本文中，显示了通过使用几种不同的 L-氨基酸作为合成子获得的短修饰肽核酸 (PNA) 的合成。该合成是通过亚单体策略进行的，获得模型三聚体 PNA，其骨架中含有嵌入的氨基酸衍生侧链，模拟肽序列 PKKKRKV，这是一种广泛用于将货物分子转运到细胞核中的核定位信号 (NLS)。荧光实验表明，这种修饰的 PNA，而不是具有相同核碱基序列的标准未修饰的 PNA，能够穿透横纹肌肉瘤细胞核，其行为与 NLS 标准肽完全相同。
• Peptide nucleic acids having 2,6-diaminopurine nucleobases
  申请人：——

  公开号：US06414112B1

  公开（公告）日：2002-07-02

  A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and binding affinity. The peptide nucleic acids of the invention comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone. Some PNAs of the invention also contain C1-C8 alkylamine side chains.

  一种新型化合物类别，被称为肽核酸，比相应的DNA链和RNA链结合更牢固，并表现出增强的序列特异性和结合亲和力。该发明的肽核酸包括从天然存在的核碱基和连接到聚酰胺骨架的非天然核碱基中选择的配体。该发明的一些肽核酸还包含C1-C8烷基胺侧链。
• Peptide nucleic acids
  申请人：——

  公开号：US05539082A1

  公开（公告）日：1996-07-23

  A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

  一种新型化合物，被称为肽核酸，比相应的DNA更强烈地结合互补的单链DNA和RNA链。肽核酸通常包括配体，例如天然存在的DNA碱基，通过适当的连接剂连接到肽骨架上。
• Peptide nucleic acids having enhanced binding affinity, sequence
  申请人：——

  公开号：US05714331A1

  公开（公告）日：1998-02-03

  A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone, and contain C.sub.1 -C.sub.8 alkylamine side chains. Methods of enhancing the solubility, binding affinity and sequence specificity of PNAs are provided.

  一种新型化合物，被称为肽核酸，比相应的DNA链和RNA链结合更牢固，并表现出增强的序列特异性和溶解性。肽核酸包括从天然存在的核碱基和连接到聚酰胺骨架的非天然存在的核碱基中选择的配体，并含有C.sub.1 -C.sub.8烷基胺侧链。提供了增强PNAs溶解性、结合亲和力和序列特异性的方法。
• Double-stranded peptide nucleic acids
  申请人：——

  公开号：US06228982B1

  公开（公告）日：2001-05-08

  A novel class of compounds, known as peptide nucleic acids, form double-stranded structures with one another and with ssDNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

  一种新型化合物，被称为肽核酸，彼此之间和与单链DNA形成双链结构。肽核酸通常包括配体，例如天然存在的DNA碱基，通过适当的连接剂连接到肽骨架上。