L-DOPA dioxygenase is an extradiol enzyme that cleaves the aromatic ring of catechols, yet there is limited research on how it functions. L-DOPA dioxygenase is part of the structural family of vicinal oxygen chelate (VOC) dioxygenases, a superfamily containing a metal coordination environment to promote direct electrophilic participation of the metal ion in catalysis. To help identify the catalytic rate and mechanism of L-DOPA dioxygenase, a variety of dopamine and L-DOPA analogs were synthesized using an electrophilic aromatic substitution as a key reaction to install a substituent on the ring. In this project specifically, 6-carboxydopamine was synthesized in five steps to produce an overall  8.2% percent yield. The synthesis of this compound and other L-DOPA derivatives will be discussed.

Synthesis of dopamine and L-DOPA analogs to investigate enzymatic function of L-DOPA dioxygenase

ACS Spring Meeting 2021

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