Enantiomeric self-aggregation of zinc 132-methyl-bacteriochlorophyll-d analogs with a porphyrin π-skeleton

Zinc dodecyl 3-hydroxymethyl-(132R/S)-methyl-pyroprotopheophorbide-a enantiomers self-aggregated in an aqueous Triton X-100 micellar solution to give chlorosome-like J-aggregates. The chiral supramolecules of the resulting zinc porphyrin self-aggregates were dependent on the stereochemistry of the asymmetric carbon atom at the 132-position. The chiral and steric effects near the 13-carbonyl group on the aggregation confirmed that the 131-oxo group hydrogen-bonded with the 31-OH group, which was requisite for the in vivo production of the chlorosomal aggregates.