5-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methylfuro[3,2-c]pyridine-4(5H)-thione | 1472655-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 5-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methylfuro[3,2-c]pyridine-4(5H)-thione
• CAS: 1472655-12-1
• 化学式: C₁₃H₁₅NO₄S
• 分子量: 281.332
• InChiKey: FJRYYBQXVTYQIM-MVWJERBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  67.76
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methylfuro[3,2-c]pyridine-4(5H)-thione 在 磷酸三甲酯 、 三氯氧磷 、 三正丁胺 、 三丁基焦磷酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以10%的产率得到dFPT1TP
  参考文献：
  名称：

  Natural-like Replication of an Unnatural Base Pair for the Expansion of the Genetic Alphabet and Biotechnology Applications

  摘要：

  We synthesized a panel of unnatural base pairs whose pairing depends on hydrophobic and packing forces and identify dTPT3-dNaM, which is PCR amplified with a natural base pair-like efficiency and fidelity. In addition, the dTPT3 scaffold is uniquely tolerant of attaching a propargyl amine linker, resulting in the dTPT3(PA)-dNaM pair, which is amplified only slightly less well. The identification of dTPT3 represents significant progress toward developing an unnatural base pair for the in vivo expansion of an organism's genetic alphabet and for a variety of in vitro biotechnology applications where it is used to site-specifically label amplified DNA, and it also demonstrates for the first time that hydrophobic and packing forces are sufficient to mediate natural-like replication.

  DOI：

  10.1021/ja408814g
• 作为产物：
  描述：

  (2E)-3-(5-甲基-2-呋喃基)丙烯酸 在 劳森试剂 、 甲醇 、 氯化亚砜 、 sodium azide 、 N,O-双三甲硅基乙酰胺 、 sodium methylate 作用下， 以 1,4-二氧六环 、 二苯醚 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.17h， 生成 5-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methylfuro[3,2-c]pyridine-4(5H)-thione
  参考文献：
  名称：

  Natural-like Replication of an Unnatural Base Pair for the Expansion of the Genetic Alphabet and Biotechnology Applications

  摘要：

  We synthesized a panel of unnatural base pairs whose pairing depends on hydrophobic and packing forces and identify dTPT3-dNaM, which is PCR amplified with a natural base pair-like efficiency and fidelity. In addition, the dTPT3 scaffold is uniquely tolerant of attaching a propargyl amine linker, resulting in the dTPT3(PA)-dNaM pair, which is amplified only slightly less well. The identification of dTPT3 represents significant progress toward developing an unnatural base pair for the in vivo expansion of an organism's genetic alphabet and for a variety of in vitro biotechnology applications where it is used to site-specifically label amplified DNA, and it also demonstrates for the first time that hydrophobic and packing forces are sufficient to mediate natural-like replication.

  DOI：

  10.1021/ja408814g

文献信息

• [EN] A METHOD FOR THE SITE-SPECIFIC ENZYMATIC LABELLING OF NUCLEIC ACIDS IN VITRO BY INCORPORATION OF UNNATURAL NUCLEOTIDES<br/>[FR] PROCÉDÉ D'ÉTIQUETAGE ENZYMATIQUE SPÉCIFIQUE DE SITE D'ACIDES NUCLÉIQUES IN VITRO PAR INCORPORATION DE NUCLÉOTIDES NON NATURELS
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2015021432A1

  公开（公告）日：2015-02-12

  Provided herein are analogs of unnatural nucleotides bearing predominantly hydrophobic nucleobase analogs that form unnatural base pairs during DNA polymerase- mediated replication of DNA or RNA polymerase-mediated transcription of RNA. In this manner, the unnatural nucleobases can be introduced in a site-specific way into oligonucleotides (single or double stranded DNA or RNA), where they can provide for site-specific cleavage, or can provide a reactive linker than can undergo functionalization with a cargo -bearing reagent by means of reaction with a primary amino group or by means of click chemistry with an alkyne group of the unnatural nucleobase linker.

  本文提供了一些不自然核苷酸的类似物，主要带有疏水性核碱基类似物，这些类似物在DNA聚合酶介导的DNA复制或RNA聚合酶介导的RNA转录过程中形成不自然碱基对。通过这种方式，可以将这些不自然碱基以特定位置的方式引入寡核苷酸（单链或双链DNA或RNA）中，从而可以实现特定位置的切割，或者可以提供一个反应性连接物，通过与主要氨基团反应或与不自然碱基连接物的炔基团进行点击化学反应，从而实现与携带试剂的载体的官能化。