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

The Journal of Organic Chemistry
Michio Kunieda, Hitoshi Tamiaki

Abstract

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.

References

Jan 9, 1999·Bioorganic & Medicinal Chemistry·H TamiakiT Miyatake
Oct 12, 2002·The Journal of Organic Chemistry·Masahiko TaniguchiJonathan S Lindsey
Apr 14, 2005·Chemical Reviews·Freek J M HoebenAlbertus P H J Schenning
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Aug 18, 2005·Accounts of Chemical Research·Teodor Silviu Balaban
Mar 8, 2006·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Tadashi MizoguchiHitoshi Tamiaki
Jul 5, 2007·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Reiko ShibataHitoshi Tamiaki
Aug 21, 2007·The Journal of Organic Chemistry·Michio KuniedaHitoshi Tamiaki

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