1H and 13C NMR Assignments for the Cyanine Dyes SYBR Safe and Thiazole Orange

Analysis of 1H and 13C NMR and mass spectral data for the fluorescent nucleic acid stain SYBR Safe indicates that it contains a cyanine-based cationic core structure identical to thiazole orange. The difference between these two compounds is the type of N-substitution on the quinolinium ring system...

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Veröffentlicht in:Journal of organic chemistry 2012-12, Vol.77 (23), p.10967-10971
Hauptverfasser: Evenson, William E, Boden, Lauren M, Muzikar, Katy A, O’Leary, Daniel J
Format: Artikel
Sprache:eng
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Zusammenfassung:Analysis of 1H and 13C NMR and mass spectral data for the fluorescent nucleic acid stain SYBR Safe indicates that it contains a cyanine-based cationic core structure identical to thiazole orange. The difference between these two compounds is the type of N-substitution on the quinolinium ring system (SYBR Safe, n-Pr; thiazole orange, Me). The 1H and 13C NMR resonances for both compounds were assigned on the basis of one- and two-dimensional (COSY, ROESY, HSQC, and HMBC) experiments. The preferred conformation of these compounds was computed by ab initio methods and found to be consistent with the NMR data.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3021659