Synthesis of zinc 3-hydroxymethyl-porphyrins possessing carbonyl groups at the 13- and/or 15-positions for models of self-aggregative chlorophylls in green photosynthetic bacteria.
Zinc 3-hydroxymethyl-protopyropheophorbide-d derivatives 1, 2, and 3 possessing carbonyl group(s) at the 13/15-, 13-, and 15-positions, respectively, and 4 lacking the C=O group were prepared from naturally occurring chlorophyll-a. Zinc porphyrins 1 and 2 possessing the 13-C=O self-aggregated in an aqueous micellar solution, similarly to the self-aggregates of BChls-c/d/e in the main light-harvesting antenna systems of green photosynthetic bacteria, whereas 3 and 4 lacking the 13-C=O failed to make such well-ordered aggregates. These results indicated that both the presence of the C=O group and its situation at the 13-position were preferable for formation of the well-ordered J-aggregates.
Kunieda
Michio
M
Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
Tamiaki
Hitoshi
H
D001429:Bacteriochlorophylls / Q000737:chemistry*; D041862:Chloroflexi / Q000737:chemistry*; D008665:Metalloporphyrins / Q000138:chemical synthesis*; D008823:Micelles; D008958:Models, Molecular; D018716:Molecular Mimicry; D015032:Zinc
D001429:Bacteriochlorophylls; D008665:Metalloporphyrins; D008823:Micelles; D015032:Zinc