Synthesis of a chlorin with annelated lactam ring as subunit for artificial photosynthetic reaction centres

Franz-Peter Montforts, Elmar Haake, John Arthur Joule
2018 ARKIVOC  
A chlorin with an annelated cyclic ketone moiety was synthesized from a tricyclic nickel complex and appropriate pyrrole building blocks. Ketone functionality of the target chlorin allows Beckmann rearrangement to yield chlorin lactams. Lactam moieties on the chlorin represent masked amino acid structures which should allow formation of peptide-like backbones, along which chlorin pigments are arranged. Due to the "natural" chlorin chromophores and the peptide backbone the devices should
more » ... ices should represent artificial mimetics of natural photosynthesis systems. N HN N CH 3 CH 3 CH 3 CH 3 NH H 3 C H 3 C N H O 13a To obtain more biomimetic photosynthesis models we aimed at the synthesis of chlorin type pigments with amino acid functionality. The chlorin subunits could then be covalently linked to peptide-like oligomers using established coupling methods from peptide chemistry (Figure 2) . Chlorin pigments arranged along the artificial peptide backbone could mimic the natural design in which chlorophylls are held together by lipophilic interactions with the protein environment.
doi:10.24820/ark.5550190.p010.463 fatcat:xrcqqisk4vgrxbv6cbqefkxbxu