Synthesis of zinc bacteriochlorophyll-d analogues with various 17-substituents and their chlorosomal self-aggregates in non-polar organic solvents.

@article{Tamiaki2008SynthesisOZ,
  title={Synthesis of zinc bacteriochlorophyll-d analogues with various 17-substituents and their chlorosomal self-aggregates in non-polar organic solvents.},
  author={Hitoshi Tamiaki and Tomotaka Michitsuji and Reiko Shibata},
  journal={Photochemical \& photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology},
  year={2008},
  volume={7 10},
  pages={
          1225-30
        }
}
  • H. Tamiaki, Tomotaka Michitsuji, R. Shibata
  • Published 17 September 2008
  • Chemistry
  • Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology
Zinc 3(1)-demethyl-bacteriopheophorbides-d possessing various 17-propionate residue (17(2)-COOCH2-) were prepared as models of light-harvesting pigments in major photosynthetic antennae of green bacteria. The synthetic compounds were monomeric in polar organic solvents to give the same visible absorption spectra, but self-aggregated in non-polar organic solvents to afford large oligomers with broadened and red-shifted absorption bands. The peak positions were identical for all the self… 
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17 Citations

17 Citations

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Citation Type

Synthesis of 32-substituted bacteriochlorophyll-d analogs and their self-aggregation in a nonpolar organic solvent
Self-assembly of zinc chlorophyll derivatives possessing a pyrenyl group at the 17-propionate residue and effects of additional γ-cyclodextrins on their optical properties
Two kinds of zinc 31-hydroxy-131-oxo-chlorins 1 and 2 possessing a pyrenyl group at the 17-propionate residue, of which the linker length between the chlorin and the pyrene moieties was varied, were…
Synthesis and self-assembly of amphiphilic zinc chlorophyll derivatives possessing a crown ether at the 17-propionate residue
Synthesis of galactosylated zinc bacteriochlorophyll-d analogs and their self-aggregation in an aqueous methanol solution
Construction of chlorosomal rod self-aggregates in the solid state on any substrates from synthetic chlorophyll derivatives possessing an oligomethylene chain at the 17-propionate residue.
TLDR
The supramolecular formation and stability of the rod on the examined substrates depended on the length of an oligomethylene chain at the 17-propionate residue as well as on the surface properties.
Mimics of the self-assembling chlorosomal bacteriochlorophylls: regio- and stereoselective synthesis and stereoanalysis of acyl(1-hydroxyalkyl)porphyrins.
TLDR
Self-assembly of a variety of these zinc BChl d mimics proves that a collinear arrangement of the hydroxyalkyl substituent with the zinc atom and the carbonyl substituents is not a stringent requirement, since both the 3,13 and the 3-17 regioisomers self-assemble readily as the racemates.
Temperature-dependent spectral changes of self-aggregates of zinc chlorophylls esterified by different linear alcohols at the 17-propionate
Systematically synthetic zinc 3-hydroxymethyl-131-oxo-chlorins esterified by different linear alcohols (methanol, 1-propanol, 1-hexanol, 1-dodecanol and 1-octadecanol) at the 17-propionate were…
In vitro self-assembly of bacteriochlorophyll c derivatives monoesterified with α,ω-diols isolated from the green sulfur photosynthetic bacterium Chlorobaculum tepidum
TLDR
In vitro assembling behaviours of unnatural BChls c isolated from Cba.
Synthesis, spectroscopic, and in vitro photosensitizing efficacy of ketobacteriochlorins derived from ring-B and ring-D reduced chlorins via pinacol-pinacolone rearrangement.
TLDR
A regioselective oxidation of a series bacteriochlorins, which on reacting with either ferric chloride or 2,3-dichloro-5,6-dicyanobenzoquinone yielded the corresponding ring-B or ring-D reduced chlorins, shows strong long-wavelength absorption and produced significant in vitro photosensitizing ability.
Synthesis of meso-tetraarylporphyrins possessing amino and carboxy groups and their peptides
TLDR
The N-(9-fluorenyl)-methyloxycarbonyl compound, Fmoc-Phe(p-P)-OH, was synthesized without any loss of enantiomeric purity (based on chiral HPLC analysis) from commercially available L-tyrosine and was useful for preparation of the peptides in both liquid and solid phases.
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References

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  • Chemistry
    Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology
  • 2007
TLDR
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TLDR
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lines of the doublet was about five times that of the singlet at the approximate center of the doublet corresponding to [l3C,I4N]-labeled molecules. One can therefore conclude that n-octylamine is…
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