189748-84-3Relevant articles and documents
Flavin-Based Light-Driven Fluorescent Probe for the Detection of Antioxidant Amino Acids
Hong, Kyeong-Im,Lee, Seong Min,Jang, Woo-Dong
, p. 57 - 60 (2018)
We have synthesized a flavin-N(5)-oxide derivative with a p-toluenesulfonyl (Ts-OF) group as a “turn-on” fluorescent probe for the detection of several antioxidant amino acids and biothiols. Oxidized flavin was synthesized by using dithiothreitol as the reducing agent. Ts-OF showed a light-driven fluorescence enhancement in the presence of several amino acids and biothiols such as histidine (His), methionine (Met), cysteine (Cys), glutathione (GSH), and homocysteine (Hcy). The 1H NMR study indicated the reductive elimination of the p-toluenesulfonyl group from Ts-OF in the presence of antioxidants and photo-irradiation.
Method for preparing new flavin derivatives: Synthesis of flavin-thymine nucleotides and flavin-oligonucleotide adducts
Frier, Christelle,Decout, Jean-Luc,Fontecave, Marc
, p. 3520 - 3528 (2007/10/03)
In order to link to the 5'-end of oligonucleotides the flavin analogs 9a,b possessing only one terminal hydroxy group on the side chain, the phosphoramidite and the H-phosphonate coupling methods were developed. Surprisingly, after reaction of compounds 9a,b with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, the flavin phosphoramidates 11a,b were isolated instead of the expected phosphoramidite derivatives 10a,b. A very efficient photooxidation process occurred probably during the isolation of the products. From the prepared flavin H-phosphonates 12a,b, flavin-thymine nucleotides and flavin-oligonucleotide adducts were synthesized for the first time. The versatility of the method was demonstrated in the oxidation step with the synthesis of the flavin-thymine nucleotides 15-17 possessing a phosphodiester, a phosphorothioate, and a methyl phosphate linkage, respectively. This method is of general interest with regard to the extensive research developed for preparing flavin analogs and modified oligonucleotides possessing interesting biological or/and catalytic properties.