A facile synthetic method for conversion of chlorophyll-a to bacteriochlorophyll-c.
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.
Sasaki
Shin-Ichi
S
Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
Mizoguchi
Tadashi
T
Tamiaki
Hitoshi
H
D001426:Bacterial Proteins / Q000138:chemical synthesis*; D001429:Bacteriochlorophylls / Q000138:chemical synthesis*; D002734:Chlorophyll / Q000737:chemistry*; D000077194:Chlorophyll A; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism
D001426:Bacterial Proteins; D001429:Bacteriochlorophylls; D002734:Chlorophyll; C002084:bacteriochlorophyll c; D000077194:Chlorophyll A