“…ESI-TOF: m / z calcd for 22 C 6 H 5 N 3 O [M + Na] + 158.0325, found 158.0331; m / z calcd for 23 C 6 H 7 N 3 O 2 [M + Na] + 176.0430, found 176.0438. The obtained NMR data correspond to literature values reported earlier. , …”
Section: Methodssupporting
confidence: 90%
“…In the case of eth dC ( 2 ), the situation is different. Here, acid treatment led to cleavage of the N -glycosylic bond and formation of a 1:1 mixture of 5-ethynylcytosine ( 22 ) and 5-acetylcytosine ( 23 ) in 84% overall yield. Both components were identified by NMR spectra and mass data.…”
Clickable oligonucleotides with ethynyl residues in the 5-position of pyrimidines ((eth)dC and (eth)dU) or the 7-position of 7-deazaguanine ((eth)c(7)G(d)) are hydrated during solid-phase oligonucleotide synthesis and workup conditions. The side products were identified as acetyl derivatives by MALDI-TOF mass spectra of oligonucleotides and by detection of modified nucleosides after enzymatic phosphodiester hydrolysis. Ethynyl → acetyl group conversion was also studied on ethynylated nucleosides under acidic and basic conditions. It could be shown that side chain conversion depends on the nucleobase structure. Triisopropylsilyl residues were introduced to protect ethynyl residues from hydration. Pure, acetyl group free oligonucleotides were isolated after desilylation in all cases.
“…ESI-TOF: m / z calcd for 22 C 6 H 5 N 3 O [M + Na] + 158.0325, found 158.0331; m / z calcd for 23 C 6 H 7 N 3 O 2 [M + Na] + 176.0430, found 176.0438. The obtained NMR data correspond to literature values reported earlier. , …”
Section: Methodssupporting
confidence: 90%
“…In the case of eth dC ( 2 ), the situation is different. Here, acid treatment led to cleavage of the N -glycosylic bond and formation of a 1:1 mixture of 5-ethynylcytosine ( 22 ) and 5-acetylcytosine ( 23 ) in 84% overall yield. Both components were identified by NMR spectra and mass data.…”
Clickable oligonucleotides with ethynyl residues in the 5-position of pyrimidines ((eth)dC and (eth)dU) or the 7-position of 7-deazaguanine ((eth)c(7)G(d)) are hydrated during solid-phase oligonucleotide synthesis and workup conditions. The side products were identified as acetyl derivatives by MALDI-TOF mass spectra of oligonucleotides and by detection of modified nucleosides after enzymatic phosphodiester hydrolysis. Ethynyl → acetyl group conversion was also studied on ethynylated nucleosides under acidic and basic conditions. It could be shown that side chain conversion depends on the nucleobase structure. Triisopropylsilyl residues were introduced to protect ethynyl residues from hydration. Pure, acetyl group free oligonucleotides were isolated after desilylation in all cases.
“…In this study, the 2-arylidene-3-oxobutanenitrile derivatives 2 used for the current studies were easily prepared by the Knoevenagel condensation between aldehydes and 3-oxobutanenitrile 1 [10], which was obtained by acid hydrolysis of b-aminocrotononitrile [11,12]. 3-Acetyl-2amino-4H-chromen-5(6H)-one derivatives 3 were synthesized by reaction of 2-arylidene-3-oxobutanenitrile 2 and 5,5-dimethyl-1,3-cyclohexanedione in ethylene glycol.…”
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.