Synthesis and Self-Assembly of Zinc Methyl Bacteriopheophorbide-f and its Homolog

Tamiaki, Hitoshi; Kubo, Masanobu; Oba, Toru

doi:10.1016/s0040-4020(00)00590-1

Cited by 47 publications

(23 citation statements)

References 48 publications

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“…The stereochemistry was determined as follows. A 3 1 -epimeric mixture of R/ S[EM]BPhe-f M was zinc-metallated and separated by RP-HPLC to give Zn-R[EM]BPhe-f M and Zn-S[EM]BPhe-f M as the first and second fractions, as had been fully confirmed previously (Tamiaki et al 2000) (see Scheme S1). For improvement of the epimeric separation, the eluent was changed from the previous aqueous methanol to the present aqueous acetonitrile, and the epimers were eluted more rapidly and separated more distinctly in the latter than in the former: separation ratio = 0.…”

Section: Resultssupporting

confidence: 73%

“…Methyl ester of metal-free bacteriopheophorbide-f possessing ethyl (E) and methyl (M) groups at the 8-and 12-positions, respectively, (=[EM]BPhe-f M , see Scheme 2) has already been reported to be synthesized from Chls-a (Tamiaki et al 1999) and b (Risch et al 1988;Simpson and Smith 1988;Tamiaki et al 2000). The other homologs, [EE]-, [PE]-, and [IE]BPhes-f M (P = propyl and I = isobutyl), were also obtained from the corresponding BChld homologs (Tamiaki et al 2003).…”

Section: Introductionmentioning

confidence: 99%

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In vitro synthesis and characterization of bacteriochlorophyll-f and its absence in bacteriochlorophyll-e producing organisms

et al. 2010

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Bacteriochlorophyll(BChl)-f which has not yet been found in natural phototrophs was prepared by chemically modifying chlorophyll-b. The retention time of reverse-phase high-performance liquid chromatography of the synthetic monomeric BChl-f as well as its visible absorption and fluorescence emission spectra in a solution were identified and compared with other naturally occurring chlorophyll pigments obtained from the main light-harvesting antenna systems of green sulfur bacteria, BChls-c/d/e. Based on the above data, BChl-f was below the level of detection in three strains of green photosynthetic bacteria producing BChl-e.

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Section: Resultssupporting

confidence: 73%

Section: Introductionmentioning

confidence: 99%

In vitro synthesis and characterization of bacteriochlorophyll-f and its absence in bacteriochlorophyll-e producing organisms

et al. 2010

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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: 66%

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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“…The 14 817 cm -1 band has associated a positive CD component of appropriate width, but much smaller amplitude than the strong negative band at 14 630 cm -1 . Phenomenologically, such pronounced CD nonconservation (asymmetry) in the Q y region of chl systems can be associated with dimerization, or higher oligomer formation (53,(63)(64)(65). Simple exciton coupling theory [e.g., (54)] does not predict such an effect, but chromophore interaction-induced mixing of higher energy states (Q x , B x,y , etc) into the Q y levels can induce CD asymmetry in the Q y region (63,64).…”

Section: Discussionmentioning

confidence: 99%

Magneto-Optical Measurements of the Pigments in Fully Active Photosystem II Core Complexes from Plants

et al. 2002

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Preparation of a minimum PSII core complex from spinach is described, containing four Mn per reaction center (RC) and exhibiting high O2 evolving activity [approximately 4000 micromol of O2 (mg of chl)(-1) x h(-1)]. The complex consists of the CP47 and CP43 chlorophyll binding proteins, the RC D1/D2 pair, the cytochrome b559 subunits, and the Mn-stabilizing psbO (33 kDa) protein, all present in the same stoichiometric amounts found in the parent PSII membranes. Several small subunits are also present. The cyt b559 content is 1.0 per RC in core complexes and PSII membranes. The total chlorophyll content is 32 chl a and <1 chl b per RC, the lowest yet reported for any active PSII preparation. The core complex exhibits the characteristic EPR signals seen in the S2 state of higher plant PSII. A procedure for preparing low-temperature samples of very high optical quality is developed, allowing detailed optical studies in the S1 and S2 states of the system to be made. Optical absorption, CD, and MCD spectra reveal unprecedented detail, including a prominent, well-resolved feature at 683.5 nm (14630 cm(-1)) with a weaker partner at 187 cm(-1) to higher energy. On the basis of band intensity, CD, and MCD arguments, these features are identified as the exciton split components of P680 in an intact, active reaction center special pair. Comparisons are made with solubilized D1/D2/cyt b559 material and cyanobacterial PSII.

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Synthesis and Self-Assembly of Zinc Methyl Bacteriopheophorbide-f and its Homolog

Cited by 47 publications

References 48 publications

In vitro synthesis and characterization of bacteriochlorophyll-f and its absence in bacteriochlorophyll-e producing organisms

In vitro synthesis and characterization of bacteriochlorophyll-f and its absence in bacteriochlorophyll-e producing organisms

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

Magneto-Optical Measurements of the Pigments in Fully Active Photosystem II Core Complexes from Plants

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