Synthesis of Latia luciferin benzoate analogues and their bioluminescent activity

The bioluminescent system of the univalve shell Latia neritoides exhibits a luciferin-luciferase reaction. We study the enol formate structure of Latia luciferin, which is expected to be important for luminescent activity. The Latia luciferin analogues with an enol substituted benzoate moiety were synthesized and their bioluminescent activity was measured. The Latia luciferin benzoate analogues delay emission for natural luciferin in bioluminescence, indicating that the Latia bioluminescent activity can be controlled by the design of the enol ester.