Stereoisomeric bio-inversion key to biosynthesis of firefly D-luciferin.
The chirality of the luciferin substrate is critical to the luciferin-luciferase reaction producing bioluminescence. In firefly, the biosynthetic pathway of D-luciferin is still unclear, although it can be synthesized in vitro from D-cysteine. Here, we show that the firefly produces both D- and L-luciferin, and that the amount of active D-luciferin increases gradually with maturation stage. Studies of firefly body extracts indicate the possible conversion of L-cysteine via L-luciferin into D-luciferin, suggesting that the biosynthesis is enzymatically regulated by stereoisomeric bio-inversion of L-luciferin. We conclude that the selection of chirality in living organisms is not as rigid as previously thought.
Niwa
Kazuki
K
Research Institute for Cell Engineering, National Institute of Advanced Industrial Science and Technology, AIST, Japan.
Nakamura
Mitsuhiro
M
Ohmiya
Yoshihiro
Y
D000818:Animals; D048888:Fireflies / Q000737:chemistry / Q000254:growth & development*; D049454:Firefly Luciferin / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
D049454:Firefly Luciferin