Synthesis of Aminotroponyl-/Difluoroboronyl Aminotroponyl Deoxyuridine Phosphoramidites

• Published in: Current protocols Vol. 2; no. 12; p. e609
• Main Authors: Palai, Bibhuti Bhusana, Panda, Subhashree S, Sharma, Nagendra K
• Format: Journal Article
• Language: English
• Published: United States 01.12.2022
• Subjects: Deoxyuridine - chemistry; DNA - chemistry; DNA, B-Form; Oligonucleotides - chemistry; BODIPY; tropolone; DNA; nucleoside; aminotroponyl; deoxyuridine; aminotropone; difluoroboronyl aminotroponyl
• ISSN: 2691-1299
• DOI: 10.1002/cpz1.609

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 Zn Ni . 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 B/ 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).