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Usage

Uses

Used in Biochemical Research:
2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine is used as a research compound for studying its interactions with nucleic acids, particularly in the context of DNA intercalation. Its unique structure allows it to efficiently intercalate into synthetic duplex DNAs containing 7-deazaguanine in place of guanine, providing insights into the molecular mechanisms of DNA binding and potential applications in molecular biology.
Used in Fluorescence Enhancement:
In the field of fluorescence studies, 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine is used to investigate the fluorescence enhancement properties of certain DNA duplexes. When intercalated with 7-deazaguanine-duplexes, it does not exhibit the usual fluorescence enhancement observed with other intercalating agents. However, when combined with 7-deazaadenine-duplexes, it shows about 70% of the expected fluorescence enhancement, making it a valuable tool for understanding fluorescence properties in nucleic acid systems.
Used in Drug Development:
Although not explicitly mentioned in the provided materials, the unique structure and properties of 2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine suggest potential applications in drug development. Its ability to interact with nucleic acids and influence fluorescence properties could make it a promising candidate for the development of new therapeutic agents, particularly those targeting DNA or RNA-based processes.
Used in Chemical Synthesis:
2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine may also find use in chemical synthesis, as its reactive functional groups can be further modified or used as building blocks for the creation of more complex molecules. This could be particularly relevant in the synthesis of novel pharmaceuticals, agrochemicals, or other specialty chemicals that require unique structural features for their function.

InChI:InChI=1/C6H6N4O/c7-6-9-4-3(1-2-8-4)5(11)10-6/h1-2H,(H4,7,8,9,10,11)

Upstream product

• 626-46-0 2,6-diamino-4-pyrimidinone 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 

Downstream Products

• 137281-08-4 N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide 
• 1369493-16-2 7-benzyl-N⁽⁴⁾-(3-bromophenyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine 
• 1394818-93-9 C₁₈H₁₈ClIN₄O 
• 848698-31-7 C₂₁H₂₀ClN₅O 
• 1417521-00-6 C₂₂H₂₈N₆O₂ 
• 1417521-04-0 C₁₇H₂₀N₆ 
• 1417521-21-1 C₁₂H₁₈N₆ 
• 443642-39-5 2-amino-4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 443642-40-8 2-amino-4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 934524-13-7 4-chloro-7-[(4-methylbenzene)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 873792-67-7 4-chloro-5-iodo-2-(pivaloylamino)-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 

Relevant academic research and scientific papers

Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues

Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.