2-(6-amino-9H-purin-9-yl)propanoic acid | 87620-89-1

• 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-(6-amino-9H-purin-9-yl)propanoic acid
• 英文别名: 2-(6-aminopurin-9-yl)propanoic acid
• CAS: 87620-89-1
• 化学式: C₈H₉N₅O₂
• 分子量: 207.192
• InChiKey: DNFSDVZNZNHNAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(6-amino-9H-purin-9-yl)propanoic acid 在 sodium tetrahydroborate 、 正丁基锂 、 (-)-苯并四咪唑 、 三甲基乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 240.0h， 生成 (S)-9-[1-methyl-2-((diethylphosphono)methoxy)ethyl]adeninde
  参考文献：
  名称：

  一种合成替诺福韦类似物的方法

  摘要：

  本发明公开了一种合成替诺福韦类似物的方法，属于医药中间体合成技术领域。采用α‑嘌呤取代羧酸1和醇2为原料，加入溶剂、碱、酸酐，以手性(S)‑BTM为催化剂，反应后得到手性非环嘌呤核苷3，反应的对映选择性好，收率中等至优秀。手性非环嘌呤核苷3在硼氢化钠条件下还原得到手性单醇非环嘌呤核苷4，接着磷酸化反应生成替诺福韦类似物5。本发明原料易得，操作简单，为替诺福韦(Tenofovir)类似物的合成提供了一种新途径。

  公开号：

  CN109369720B
• 作为产物：
  描述：

  ethyl 2-(adenin-9-yl)propanoate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以73%的产率得到2-(6-amino-9H-purin-9-yl)propanoic acid
  参考文献：
  名称：

  动态动力学拆分α-嘌呤取代的烷酸：获得手性无环嘌呤核苷。

  摘要：

  报道了通过α-嘌呤取代的链烷酸的动态动力学拆分来构建手性无环嘌呤核苷类似物的有效途径。使用（S）-BTM作为催化剂，可以以中等至良好的收率（高达93％）和高的对映选择性（高达98％ee）获得各种手性无环嘌呤核苷类似物。可以通过还原反应从酯化产物中获得手性无环嘌呤核苷，然后将其转移到替诺福韦类似物中。

  DOI：

  10.1021/acs.orglett.8b03555

文献信息

• PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS
  申请人：Liu Chuan Fa

  公开号：US20110245458A1

  公开（公告）日：2011-10-06

  Disclosed is a peptide nucleic acid monomer as well as a corresponding peptide nucleic acid molecule. The monomer comprises a terminal amino group and a terminal group A. The terminal amino group and the terminal group A are connected by an aliphatic moiety. The main chain of this aliphatic moiety is free of groups that are charged under physiological conditions. The terminal group A is one of —COOH, —COOR 3 , —COX, —COSR 3 , —CN, —CONH 2 , —CONHR 3 , —CONR 3 , R 4 , with R 3 and R4 being H or an aliphatic, alicyclic, aromatic, arylaliphatic or arylalicyclic group, and X being a halogen atom. The terminal amino group is substituted by an aliphatic group with a main chain of at least two carbon atoms and optionally 0 to a bout 2 heteroatoms selected from the group N, O, S, Se and Si. The main chain has a polar head group Z.

  揭示了一种肽核酸单体以及相应的肽核酸分子。该单体包括一个末端氨基团和一个末端基团A。末端氨基团和末端基团A由一个脂肪族基团连接。该脂肪族基团的主链在生理条件下不带电。末端基团A是以下之一：—COOH、—COOR3、—COX、—COSR3、—CN、—CONH2、—CONHR3、—CONR3、R4，其中R3和R4为H或脂肪族、脂环、芳香、芳香脂肪或芳香脂环基团，X为卤素原子。末端氨基团被一个至少有两个碳原子的脂肪族基团取代，可选地含有0到大约2个来自N、O、S、Se和Si组的杂原子。主链具有一个极性头基团Z。
• METHOD OF MODIFYING NUCLEOTIDE CHAIN
  申请人：MATSUSHITA ELECTRIC INDUSTRIAL CO., LTD.

  公开号：EP1647592A1

  公开（公告）日：2006-04-19

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3'-terminal side thereof; and forming a functional group (for example, an aldehyde group) capable of binding to a desired modifier (for example, NH2R having an amino group) on the 3'-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3'-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3'-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.

  一种修饰核苷酸链的方法，包括让对含有特定碱基（如次黄嘌呤（Hx））的核苷酸序列具有特异性的分解酶作用于待修饰的核苷酸链（I），该核苷酸链具有在其 3'- 末端侧含有特定碱基的上述核苷酸序列；并在核苷酸链（I）的 3'末端形成能够与所需修饰剂（例如具有氨基的 NH2R）结合的官能团（例如醛基），从而将上述修饰剂结合到核苷酸链的 3'末端。使用核苷酸链作为修饰靶，该核苷酸链的 3'- 末端含有作为酶底物的特定碱基的核苷酸序列，这种方法可以只分解上述核苷酸序列部分，从而形成与所需修饰剂反应并结合的官能团。通过这种方法，核苷酸链可以直接被修饰剂修饰，从而方便地标记或连接核苷酸链。此外，当需要固定核苷酸链时，使用修饰剂作为连接剂可以实现稳定而牢固的固定。
• Method for modifying nucleotide chain
  申请人：Joko Shigeki

  公开号：US20070077629A1

  公开（公告）日：2007-04-05

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3′-terminal side thereof; and forming a functional group (for example, analdehyde group) capable of binding to a desired modifier (for example, NH 2 R having an amino group) on the 3′-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3′-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3′-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.
• METHOD FOR MODIFYING NUCLEOTIDE CHAIN
  申请人：JOKO Shigeki

  公开号：US20100291637A1

  公开（公告）日：2010-11-18

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3′-terminal side thereof; and forming a functional group (for example, an aldehyde group) capable of binding to a desired modifier (for example, NH 2 R having an amino group) on the 3′-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3′-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3′-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.
• US8129115B2
  申请人：——

  公开号：US8129115B2

  公开（公告）日：2012-03-06