Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-06-23 , DOI: 10.1016/j.tetlet.2020.152167 Yoshiki Fujiwara , Toyoho Takeda , Shin Ogasawara , Hitoshi Tamiaki
Zinc methyl 3-hydroxymethyl-(132R/S)-methyl-pyropheophorbides-a were prepared as model compounds of bacteriochlorophyll-d by the chemical modification of naturally occurring chlorophyll-a. Both the HPLC-separated 132-epimers as well as the 132-unsubstituted counterpart self-aggregated in an aqueous Triton X-100 micellar solution to form large oligomers with red-shifted electronic absorption and intense circular dichroism bands, similarly as in natural chlorosomes, the main light-harvesting antennas of photosynthetic green bacteria. The substitution with a methyl group at the 132-position did not disturb the formation of chlorosomal self-aggregates in a J-type fashion, which were slightly dependent on the stereochemistry.
中文翻译:
叶绿素a衍生物的13 2-甲基化和锌细菌叶绿素d类似物的(13 2 R / S)-立体选择性自聚集
锌甲基-3-羟甲基- (13 2 - [R /小号) -甲基- pyropheophorbides-一个制备为bacteriochlorophyll-的模型化合物d由天然存在的叶绿素化学修饰一个。HPLC分离的13 2-受体和13 2-未取代的对映体在Triton X-100胶束溶液中自聚集,形成大的低聚物,具有电子转移的红移和强烈的圆二色性谱带,与天然类似氯体,光合绿色细菌的主要集光触角。在13 2处被甲基取代-位置没有以J-型方式干扰绿体自聚集体的形成,其略微依赖于立体化学。