Photoreduction of zinc 8-vinylated chlorophyll derivative to bacteriochlorophyll-b/g analog possessing an 8-ethylidene group |
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Authors: | Hitoshi Tamiaki Meiyun Xu Takuya Tanaka Tadashi Mizoguchi |
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Affiliation: | Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan |
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Abstract: | When a pyridine solution of zinc methyl 8-vinyl-mesopyropheophorbide-a was irradiated with visible light in the presence of ethanol, ascorbic acid and diazabicylo[2.2.2]octane under nitrogen at room temperature, zinc (7R/S,8E)-8-ethylidene-bacteriochlorin was obtained via 1,4-hydrogenation. The 1,4-photoreduction is similar to the enzymatic reduction of 8-vinyl-chlorophyllides to (E)-8-ethylidene-bacteriochlorins in anoxygenic photosynthetic bacteria producing bacteriochlorophylls-b/g. The resulting zinc 8-ethylidene-bacteriochlorin was readily isomerized to the chemically more stable 8-ethyl-chlorin by further illumination. As a by-product, zinc 8-vinyl-7,8-cis-bacteriochlorin was slightly formed by photoinduced 1,2-hydrogenation of zinc 8-vinyl-chlorin. |
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