D-Luciferin, potassium salt
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D-Luciferin, potassium salt
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CAS No:
115144-35-9
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Formula:
C11H7N2KO3S2
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Chemical Name:
D-Luciferin, potassium salt
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CAS No:
Description
D-Luciferin potassium salt is the substrate of luciferases that catalyze the production of light in bioluminescent insects.
D-Luciferin, potassium salt Use and Manufacturing
Chloroluciferin (Luc-Cl) was synthesized by reacting D-luciferin with HOCl, as shown in Fig. 2B. D-Luciferin potassium salt (100mg, 0.314mmol) was dissolved in deionized water (10mL). The solution was stirred in the dark, and HOCl (208muL, 10mM) was added. The reaction's progress was monitored by HPLC. After depletion of luciferin, hydrochloric acid (2M, 20mL) was added to the mixture. The precipitate was filtered off, washed with water until washings were neutral, and dried under reduced pressure. Crude product was purified using preparative HPLC. The position of chlorination was determined based on NMR analyses: 1H NMR, (600.13MHz): delta 7.94 (1H, d, J=9.0), 7.30 (1H, d, J=9.0), 5.35 (1H, br.dd, J=10.4, 8.4), 3.75 (1H, dd, J=10.9, 10.4), 3.71 (1H, dd, J=10.9, 8.4); 13C NMR (75.47MHz): delta 171.3 (1C, s), 163.3, (1C, s), 157.4 (1C, s), 153.4 (1C), 145.7 (1C), 137.1 (1C), 123.5 (1C), 117.6 (1C), 110.5 (1C), 78.9 (1C), 35.2 (1C). The lack of a signal of proton at the carbon atom C-2, in the 1H NMR spectrum of chlorinated luciferin (Suppl. Fig. 2A), points to its replacement by the chlorine atom. The assignment has been confirmed by 13C NMR (Suppl. Fig. 2B) and 2D-NMR analyses (Suppl. Fig. 3). The 13C chemical shift of the carbon atom C-2 at 110.5ppm combined with the 3J correlation between proton atom Hb (7.3) and the carbon atom C-2 prove that the chlorine atom is located in the position C-2. The NMR spectra of chloroluciferin, including two-dimensional sequences (heteronuclear multiple bond coherence, HMBC and heteronuclear single quantum coherence, HSQC) are shown in Supplementary Figs. 2 and
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