J. Biol. Chem., Vol. 261, Issue 19, 8593-8596, Jul, 1986
The porphinedione structure of heme d1. Synthesis and spectral properties of model compounds of the prosthetic group of dissimilatory nitrite reductase
CK Chang and W Wu
In an attempt to verify the recent proposal that the heme d1 prosthetic
group isolated from cytochrome cd1 is not a chlorin, but a dioxo-
isobacteriochlorin (Chang, C. K. (1985) J. Biol. Chem. 260, 9520-9522), a
model dioxo-isobacteriochlorin has been synthesized possessing a pi-
electron system exactly identical to that as proposed. The presence of an
acrylic acid substituent strongly perturbs the absorption spectrum of the
chromophore and produces a visible spectrum virtually indistinguishable
from that of the iron-free heme d1. Based on this finding, buttressed by
additional spectral correspondence between the model iron heme and heme d1,
we conclude that the proposed diketo ring structure is indeed correct, and
the trivial names "dioneheme" and "acryloporphyrindione" are suggested for
heme d1 and the demetallated macrocycle, respectively.
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