Fatty acid photodecarboxylase (FAP) is a photoenzyme with potential green
chemistry applications. By combining static, time-resolved, and cryotrapping
spectroscopy and crystallography as well as computation, we characterized
Chlorella variabilis FAP reaction intermediates on
time scales from subpicoseconds to milliseconds. High-resolution crystal
structures from synchrotron and free electron laser x-ray sources highlighted an
unusual bent shape of the oxidized flavin chromophore. We demonstrate that
decarboxylation occurs directly upon reduction of the excited flavin by the fatty
acid substrate. Along with flavin reoxidation by the alkyl radical intermediate, a
major fraction of the cleaved carbon dioxide unexpectedly transformed in 100
nanoseconds, most likely into bicarbonate. This reaction is orders of magnitude
faster than in solution. Two strictly conserved residues, R451 and C432, are
essential for substrate stabilization and functional charge transfer.
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