D -luciferin

Structural formula
General
Surname	D-luciferin
other names	D - (-) - luciferin; ( S ) -2- (6-Hydroxy-2-benzothiazolyl) -2-thiazoline-4-carboxylic acid; 4,5-dihydro-2- (6-hydroxy-2-benzothiazolyl) -4-thiazolecarboxylic acid; Firefly Luciferin;
Molecular formula	C 11 H 8 N 2 O 3 S 2
External identifiers / databases
EC number	219-981-3
ECHA InfoCard	100.018.166
PubChem	92934
ChemSpider	16735812
Wikidata	Q63390514
properties
Molar mass	280.32 g mol −1
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

D- luciferin (also firefly luciferin ) is a chemical compound from the group of luciferins , which are used in bioluminescent organisms to generate light. In biochemistry , luciferin is used as a substrate for the reporter enzyme luciferase .

properties

In fireflies is D luciferin in the peroxisomes, are formed of the cells of the luminous body and oxidatively decarboxylated to generate light.

Decarboxylation of the oxidized D -luciferin

The D- luciferin is oxidatively decarboxylated to oxyluciferin (oxy-L) by the enzyme luciferase in the course of bioluminescence :

{\ displaystyle \ mathrm {LH_ {2} + O_ {2} + ATP {\ xrightarrow [{Mg ^ ​​{2 +}}] {Luciferase}} \ oxy {\ text {-}} L + CO_ {2} + AMP + PP_ {i} + h \ nu}}

The reaction takes place in vitro at an optimum pH of 7.8 at room temperature. While the color of the bioluminescence in vivo is yellow-green to yellow (552-582 nm), the spectrum is larger in vitro . At an acidic pH there is a shift into the red spectrum (615 nm). It also absorbs light at 327 nm and emits fluorescence at 530 nm.

The biosynthesis of D - and L luciferin is carried out from two cysteines , and p-benzoquinone or hydroquinone . The chemical synthesis takes place analogously.

Biosynthesis in Luciola lateralis

Applications

D- luciferin is used in conjunction with the use of luciferases as a reporter gene .

Individual evidence

↑ ^a ^b ^c data sheet D-Luciferin, from Sigma-Aldrich , accessed on December 18, 2017 ( PDF ).
↑ GA Keller, S. Gould, M. Deluca, S. Subramani: Firefly luciferase is targeted to peroxisomes in mammalian cells. In: Proceedings of the National Academy of Sciences of the United States of America . Volume 84, Number 10, May 1987, pp. 3264-3268, PMID 3554235 , PMC 304849 (free full text).
↑ Y. Oba, N. Yoshida, S. Kanie, M. Ojika, S. Inouye: Biosynthesis of firefly luciferin in adult lantern: decarboxylation of L-cysteine is a key step for benzothiazole ring formation in firefly luciferin synthesis. In: PloS one . Volume 8, number 12, 2013, p. E84023, doi : 10.1371 / journal.pone.0084023 , PMID 24391868 , PMC 3877152 (free full text).
^ S. Kanie, T. Nishikawa, M. Ojika, Y. Oba: One-pot non-enzymatic formation of firefly luciferin in a neutral buffer from p-benzoquinone and cysteine. In: Scientific reports . Volume 6, April 2016, p. 24794, doi : 10.1038 / srep24794 , PMID 27098929 , PMC 4838837 (free full text).
↑ L. Pinto da Silva, JC Esteves da Silva: Firefly luciferin as a multifunctional chemiluminescence molecule. In: Photochemical & photobiological sciences: Official journal of the European Photochemistry Association and the European Society for Photobiology. Volume 12, Number 9, September 2013, pp. 1615-1621, doi : 10.1039 / c3pp50086a , PMID 23712132 .
↑ J. Vieira, L. Pinto da Silva, JC Esteves da Silva: Advances in the knowledge of light emission by firefly luciferin and oxyluciferin. In: Journal of photochemistry and photobiology. B, Biology. Volume 117, December 2012, pp. 33-39, doi : 10.1016 / j.jphotobiol.2012.08.017 , PMID 23026386 .

[Sigma-1] ta sheet D-Luciferin, from Sigma-Aldrich , accessed on December 18, 2017 ( PDF ).

[2] GA Keller, S. Gould, M. Deluca, S. Subramani: Firefly luciferase is targeted to peroxisomes in mammalian cells. In: Proceedings of the National Academy of Sciences of the United States of America . Volume 84, Number 10, May 1987, pp. 3264-3268, PMID 3554235 , PMC 304849 (free full text).

[3] Y. Oba, N. Yoshida, S. Kanie, M. Ojika, S. Inouye: Biosynthesis of firefly luciferin in adult lantern: decarboxylation of L-cysteine is a key step for benzothiazole ring formation in firefly luciferin synthesis. In: PloS one . Volume 8, number 12, 2013, p. E84023, doi : 10.1371 / journal.pone.0084023 , PMID 24391868 , PMC 3877152 (free full text).

[4] S. Kanie, T. Nishikawa, M. Ojika, Y. Oba: One-pot non-enzymatic formation of firefly luciferin in a neutral buffer from p-benzoquinone and cysteine. In: Scientific reports . Volume 6, April 2016, p. 24794, doi : 10.1038 / srep24794 , PMID 27098929 , PMC 4838837 (free full text).

[5] L. Pinto da Silva, JC Esteves da Silva: Firefly luciferin as a multifunctional chemiluminescence molecule. In: Photochemical & photobiological sciences: Official journal of the European Photochemistry Association and the European Society for Photobiology. Volume 12, Number 9, September 2013, pp. 1615-1621, doi : 10.1039 / c3pp50086a , PMID 23712132 .

[6] J. Vieira, L. Pinto da Silva, JC Esteves da Silva: Advances in the knowledge of light emission by firefly luciferin and oxyluciferin. In: Journal of photochemistry and photobiology. B, Biology. Volume 117, December 2012, pp. 33-39, doi : 10.1016 / j.jphotobiol.2012.08.017 , PMID 23026386 .