title: Introduction of perfluoroalkyl chain into the esterifying moiety of bacteriochlorophyll c in the green sulfur photosynthetic bacterium Chlorobaculum tepidum by pigment biosynthesis.
abstract: The green sulfur photosynthetic bacterium Chlorobaculum (Cba.) tepidum was grown in liquid cultures containing perfluoro-1-decanol, 1H,1H,2H,2H-heptadecafluoro-1-decanol [CF3(CF2)7(CH2)2OH] or 1H,1H-nonadecafluoro-1-decanol [CF3(CF2)8CH2OH], to introduce rigid and fluorophilic chains into the esterifying moiety of light-harvesting bacteriochlorophyll (BChl) c. Exogenous 1H,1H,2H,2H-heptadecafluoro-1-decanol was successfully attached to the 17(2)-carboxy group of bacteriochlorophyllide (BChlide) c in vivo: the relative ratio of the unnatural BChl c esterified with this perfluoroalcohol over the total BChl c was 10.3%. Heat treatment of the liquid medium containing 1H,1H,2H,2H-heptadecafluoro-1-decanol with β-cyclodextrin before inoculation increased the relative ratio of the BChl c derivative esterified with this alcohol in the total BChl c in Cba. tepidum. In a while, 1H,1H-nonadecafluoro-1-decanol was not attached to BChlide c in Cba. tepidum, which was grown by its supplementation. These results suggest that the rigidity close to the hydroxy group of the esterifying alcohol is not suitable for the recognition by the BChl c synthase called BchK in Cba. tepidum. The unnatural BChl c esterified with 1H,1H,2H,2H-heptadecafluoro-1-decanol participated in BChl c self-aggregates in chlorosomes.
authors.affiliation: Department of Chemistry, Faculty of Science and Engineering, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan; PRESTO, Japan Science and Technology Agency, Kawaguchi, Saitama 332-0012, Japan. Electronic address: saga@chem.kindai.ac.jp.
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Saga
authors.affiliation: Department of Chemistry, Faculty of Science and Engineering, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Hayato
authors.initials: H
authors.lastname: Yamashita
authors.affiliation: Department of Chemistry, Faculty of Science and Engineering, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan.
authors.forename: Keiya
authors.initials: K
authors.lastname: Hirota
mesh_terms: D001426:Bacterial Proteins / Q000096:biosynthesis* / Q000737:chemistry / Q000302:isolation & purification; D001429:Bacteriochlorophylls / Q000096:biosynthesis* / Q000737:chemistry / Q000302:isolation & purification; D019414:Chlorobi / Q000378:metabolism*; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D005233:Fatty Alcohols / Q000737:chemistry; D005466:Fluorocarbons / Q000737:chemistry*; D045342:Light-Harvesting Protein Complexes / Q000737:chemistry; D010860:Pigments, Biological / Q000096:biosynthesis* / Q000737:chemistry / Q000302:isolation & purification; D013696:Temperature; D047392:beta-Cyclodextrins / Q000737:chemistry
chemical_list: D001426:Bacterial Proteins; D001429:Bacteriochlorophylls; D004952:Esters; D005233:Fatty Alcohols; D005466:Fluorocarbons; D045342:Light-Harvesting Protein Complexes; D010860:Pigments, Biological; D047392:beta-Cyclodextrins; C033729:fluorotelomer alcohols; C002084:bacteriochlorophyll c; C031215:betadex
keywords: Bacteriochlorophyll; Biosynthesis; Chlorosome; Perfluoroalkyl group; Photosynthetic bacteria