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SYNTHESIS OF A HIGH QUANTUM YIELD ISOMORPHIC ADENOSINE ANALOG AND ITS APPLICATION FOR THE PREPARATION OF A DUALLY FLUORESCENT FAD ANALOG
Russel, Nadim Shahriar
Russel, Nadim Shahriar
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2023-12
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Chemistry
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http://dx.doi.org/10.34944/dspace/10301
Abstract
Fluorescent nucleobase analogs (FBAs) are useful tools for the study of nucleic acid dynamics and the interaction of biomolecules. To be an effective FBA, the analog should mimic the size and interactions of natural nucleobases. Redshifted absorption and emission with high quantum yield of FBAs are also desirable because these properties differentiate FBAs from natural nucleobases using optical spectroscopy. Many FBAs have been reported, but among them 2-aminopurine (2AP) is the most popular because of its high quantum yield. Recently an alternative fluorescent bas analog 8-vinyl adenine (8VA) has been discovered which has a greater quantum yield than 2AP. Here I have synthesized two novel FBAs, 2-amino-8-vinyl purine riboside (r2A8VP) and 2-amino-6-chloro-8-vinyl purine (2A6Cl8VP), which are hybrid analogs of 2AP and 8VA. r2A8VP and 2A6Cl8VP have been structurally characterized using NMR and LC-MS. UV/vis absorption and fluorescence spectroscopies demonstrate improved optical properties, such as redshifted absorption and emission compared to 2AP and 8VA. Also, r2A8VP possesses a higher quantum yield that either FBA. Besides, 2-aminopurine riboside triphosphate, 2ApTP, is synthesized which is used as a precursor for enzymatic synthesis of a new dually fluorescent FAD (flavin adenine dinucleotide) analog, F2ApD.
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