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Publikācija: A Simple Route to Fluorescent Nucleosides via Purine Bis-triazolyl Derivatives

Publication Type Conference paper
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language A Simple Route to Fluorescent Nucleosides via Purine Bis-triazolyl Derivatives
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Dace Cīrule
Kristers Ozols
Ērika Bizdēna
Keywords Fluorescent nucleoside, adenosine analogues, oligonucleotide labelling, fluorescent probes
Abstract Environmentally sensitive fluorescent nucleosides are attractive as reporter molecules. Herein we present the results of our research of purine nucleoside 6-amino-2-triazolylderivatives that exhibit fluorescent properties and are readily available from reaction of corresponding 2,6-bis-triazolylpurine nucleosides with amines. The N-nucleophiles suitable for SNAr reaction include even sterically hindered secondary amines, hydrazines, amino acids and thiols. In addition, 2,6-bis-triazolylpurine nucleosides readily produce peptide-nucleoside conjugates. The photophysical properties of synthesized fluorescent nucleosides were investigated. From our research in ribo-, deoxyribo- and arabino- series we concluded that the fluorescence properties of the obtained products are practically unaffected by sugar moiety. On the other hand, the emission spectra and quantum yields sensitively changed according to solvent properties. The solvatochromic properties of newly designed fluorescent nucleosides will be discussed. The fluorescent adenosine analogue N6-methyl-2-(1,2,3-triazol-1-yl)deoxyadenosine (A*) has been incorporated in trinucleotide sequence d(CA*G). Although the quenching of fluorescence was observed due to the presence of other nucleobases, the developed trinucleotide still retain experimentally useful levels of fluorescence.
Reference Cīrule, D., Ozols, K., Bizdēna, Ē. A Simple Route to Fluorescent Nucleosides via Purine Bis-triazolyl Derivatives. In: Proceedings of EuroTIDES Conference, Germany, Berlin, 16-18 November, 2015. Berlin: 2015, pp.3-4.
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ID 21082