Saga Yoshitaka, Yamashita Hayato, Hirota Keiya
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.
Department of Chemistry, Faculty of Science and Engineering, Kindai University, Higashi-Osaka, Osaka 577-8502, Japan.
Bioorg Med Chem. 2016 Sep 15;24(18):4165-4170. doi: 10.1016/j.bmc.2016.07.004. Epub 2016 Jul 5.
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.
绿色硫光合细菌嗜热绿菌（Chlorobaculum (Cba.) tepidum）在含有全氟-1-癸醇、1H,1H,2H,2H-十七氟-1-癸醇[CF3(CF2)7(CH2)2OH]或1H,1H-十九氟-1-癸醇[CF3(CF2)8CH2OH]的液体培养基中培养，以便将刚性且亲氟的链引入捕光细菌叶绿素（BChl）c的酯化部分。外源性1H,1H,2H,2H-十七氟-1-癸醇在体内成功连接到细菌叶绿素ide（BChlide）c的17(2)-羧基上：用这种全氟醇酯化的非天然BChl c在总BChl c中的相对比例为10.3%。在接种前用β-环糊精对含有1H,1H,2H,2H-十七氟-1-癸醇的液体培养基进行热处理，可提高嗜热绿菌中用这种醇酯化的BChl c衍生物在总BChl c中的相对比例。与此同时，1H,1H-十九氟-1-癸醇在通过其添加培养的嗜热绿菌中未连接到BChlide c上。这些结果表明，酯化醇羟基附近的刚性不适合嗜热绿菌中称为BchK的BChl c合酶识别。用1H,1H,2H,2H-十七氟-1-癸醇酯化的非天然BChl c参与了叶绿体中BChl c的自聚集体。
