Sasaki Shin-Ichi, Mizoguchi Tadashi, Tamiaki Hitoshi
Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.
J Org Chem. 2007 Jun 8;72(12):4566-9. doi: 10.1021/jo0703855. Epub 2007 May 12.
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.
描述了一种将叶绿素（Chl）-a转化为细菌叶绿素（BChl）-c的简单合成路线。甲基细菌脱镁叶绿素（MBPhe）-d可轻松从Chl-a获得，用三溴化吡啶鎓在20位进行选择性溴化，随后与甲基硼酸进行铃木偶联，以定量产率得到所需的MBPhe-c（20-Me）和脱溴的MBPhe-d（20-H）约4:1的混合物。分离出MBPhe-c，将17-丙酸酯基团进行酯交换（甲基→法呢基），并插入镁，成功得到天然存在的BChl-c。
