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In Vitro Reconstitution of Light-harvesting Complexes of Plants and Green Algae
Published on: October 10, 2014
A facile synthetic method for conversion of chlorophyll-a to bacteriochlorophyll-c
Shin-Ichi Sasaki1, Tadashi Mizoguchi, Hitoshi Tamiaki
1Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
Abstract:
A simple synthetic route for converting chlorophyll(Chl)-a to bacteriochlorophyll(BChl)-c is described. Methyl bacteriopheophorbide(MBPhe)-d, easily obtained from Chl-a, was selectively brominated at the 20-position with pyridinium tribromide, and the following Suzuki-coupling with methylboronic acid afforded ca. a 4:1 mixture of desired MBPhe-c (20-Me) and debrominated MBPhe-d (20-H) in quantitative yield. Separation of MBPhe-c, transesterification of the 17-propionate group (Me --> farnesyl), and magnesium insertion successfully led to naturally occurring BChl-c.
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