Synthesis of Aminotroponyl-/Difluoroboronyl Aminotroponyl Deoxyuridine Phosphoramidites.

Autor: Palai BB; School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, Jatani, Odisha, India.; Homi Bhabha National Institute (HBNI)-Mumbai, Mumbai, India., Panda SS; School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, Jatani, Odisha, India.; Homi Bhabha National Institute (HBNI)-Mumbai, Mumbai, India., Sharma NK; School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, Jatani, Odisha, India.; Homi Bhabha National Institute (HBNI)-Mumbai, Mumbai, India.
Jazyk: angličtina
Zdroj: Current protocols [Curr Protoc] 2022 Dec; Vol. 2 (12), pp. e609.
DOI: 10.1002/cpz1.609
Abstrakt: This report describes the chemical synthesis of aminotroponyl-conjugated deoxyuridine analog (at-dU) and its difluoroboron complex (dfbat-dU) and their phosphoramidites by using the versatile phosphorylating reagent 2-Cyanoethyl N,N-diisopropylchlorophosphoramidite. Tropolone is a non-benzenoid aromatic bioactive natural fluorescent molecule, possessing intramolecular charge transfer and metal chelating properties with transition metal ions such as Cu 2+/ Zn 2+/ Ni 2+ . Its synthetic derivatives, 2-aminotropones also exhibit unique bioactivities and are considered potential therapeutic drug candidate. Recently, the fluorescence properties of aminotropone has improved by complexing with difluoroboron residue that generates aminotroponyl-BODIPY analog. These could be employed for the synthesis of at-dU/dfbat-dU containing DNA oligonucleotides for designing the 11 B/ 19 F-NMR/fluorescence-based DNA probes. © 2022 Wiley Periodicals LLC. Basic Protocol 1: Synthesis of N-propargyl-2-aminotropone (2) and difluoroboronyl N-propargyl-2-aminotropone (3) molecules. Basic Protocol 2: Synthesis of N-propargyl-2-aminotroponyl deoxyuridinyl (at-dU) phosphoramidites (7). Basic Protocol 3: Synthesis of difluoroboronyl N-propargyl-2-aminotroponyl deoxyuridinyl (dfbat-dU) phosphoramidites (10).
(© 2022 Wiley Periodicals LLC.)
Databáze: MEDLINE
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