Determination of 31-stereochemistry in synthetic bacteriochlorophyll-d homologues and self-aggregation of their zinc complexes

Tamiaki, Hitoshi; Kitamoto, Hiroyuki; Nishikawa, Akiyoshi; Hibino, Takuya; Shibata, Reiko

doi:10.1016/j.bmc.2004.01.031

Cited by 47 publications

(15 citation statements)

References 27 publications

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“…Additionally, naturally occurring BChls take both R and S configurations as the 3 1 -stereochemistry. In vitro aggregates of BChls and their zinc analogues showed that their supramolecular structures were dependent on the homologues and epimers (Balaban et al , 1997Chiefari et al 1995;Ishii et al 2000;Kunieda et al 2004;Miyatake et al 2001;Mizoguchi et al 2000Mizoguchi et al , 2002Saga et al 2001;Steensgaard et al 2000;Tamiaki et al 1998Tamiaki et al , 2000Tamiaki et al , 2004. A similar observation was obtained by molecular modeling studies on self-aggregates of zinc analogues (Yagai et al 2001).…”

Section: Introductionsupporting

confidence: 59%

Time-dependent Self-assembly of 31-epimerically Pure and Mixed Zinc Methyl Bacteriopheophorbides-d in an Aqueous THF Solution

et al. 2005

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The self-aggregation process of 3(1)-epimerically pure and mixed zinc methyl bacteriopheophorbides-d (ZMBPhes-d) was examined by stopped-flow technique. A 33(v/v)% tetrahydrofuran (THF) - water solution of ZMBPhe-d was rapidly mixed with a 7(v/v)% THF - water solution to form a chlorosome-type aggregate with a red-shifted Qy band around 700 nm. We observed a rapid autocatalytic aggregation in a subsecond time scale. Aggregates of the 3(1)R epimer increased with a change in the Qy absorption maximum from 698 to 705 nm, suggesting that small aggregates formed as intermediate species. In addition, the rate of aggregation was dependent on the stereochemistry at the 3(1)-position of ZMBPhe-d; the 3(1)R epimer self-aggregated more rapidly than the 3(1)S epimer.

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Section: Introductionsupporting

confidence: 59%

Time-dependent Self-assembly of 31-epimerically Pure and Mixed Zinc Methyl Bacteriopheophorbides-d in an Aqueous THF Solution

et al. 2005

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“…12 To a dry THF solution (30 ml) of aldehyde 1a (82.5 mg, 150 mmol) was dropwise added a solution of Grignard reagent (about 10 equiv) at 0 C with stirring under nitrogen. When the Qy absorption maximum of the solution at 695 nm was hypsochromically shifted to around 665 nm, the reaction was quenched by addition of an ice-chilled aqueous 1% ammonium chloride solution (4 ml).…”

Section: Generalmentioning

confidence: 99%

Synthesis of methyl pyropheophorbide-d derivatives possessing the 3-acyl groups and their electronic absorption spectra

et al. 2016

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“…A large shift in the keto-carbonyl stretching peak (1699 À 1666 5 33 cm À1 ) by self-aggregation of porphyrin Zn-1 is comparable with shifts by the formation of C5OÁ Á ÁH-OÁ Á ÁZn in chlorin Zn-4 (1691 À 1655 5 36 cm À1 ). Therefore, Zn-1 possessing a porphyrin psystem self-aggregated to form similar supramolecular structures with in vivo and in vitro self-aggregates of chlorosomal Chls (7)(8)(9)(10)(11) and their models of synthetic chlorins including Zn-4 (13,15,27,30,31). Oligomeric Zn-1 was built by special bondings, 13-C5OÁ Á Á H-O(3 1 )Á Á ÁZn, as well as p-p interaction of composite porphyrin moieties.…”

Section: Self-aggregation Of Zinc Methyl Protobacteriopheophorbide-d mentioning

confidence: 99%

Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives¶

Tamiaki¹,

Kitamoto²,

Watanabe³

et al. 2005

Photochem Photobiol

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3(1)-Racemically pure zinc 3(1)-hydroxy-13(1)-oxo-porphyrins (zinc methyl 17,18-dehydro-bacteriopheophorbides-d) as well as their 3(1)-demethyl form were prepared by modifying chlorophyll-a through oxidation by 2,3-dichloro-5,6-dicyano-benzoquinone. From visible, circular dichroism and infrared spectral analyses, these synthetic pigments self-aggregated in 1%(vol/vol) tetrahydrofuran and cyclohexane to give large oligomers by an intermolecular bonding of 13-C=O...H-O(3(1))...Zn(central) and pi-pi interaction of the porphyrin chromophores. The supramolecular structures are similar to those of the corresponding chlorins and a core part of extramembranous light-harvesting antennas of photosynthetic green bacteria. The 17,18-dehydrogenation of a chlorin to porphyrin moiety did not disturb its self-aggregation and the synthetic zinc porphyrins are good models for naturally occurring self-aggregative bacteriochlorophylls.

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Determination of 31-stereochemistry in synthetic bacteriochlorophyll-d homologues and self-aggregation of their zinc complexes

Cited by 47 publications

References 27 publications

Time-dependent Self-assembly of 31-epimerically Pure and Mixed Zinc Methyl Bacteriopheophorbides-d in an Aqueous THF Solution

Time-dependent Self-assembly of 31-epimerically Pure and Mixed Zinc Methyl Bacteriopheophorbides-d in an Aqueous THF Solution

Synthesis of methyl pyropheophorbide-d derivatives possessing the 3-acyl groups and their electronic absorption spectra

Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives¶

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