Synthesis of a peptide-linked chlorin dyad as a model compound for the photosynthetic reaction centre.
The enantiomerically pure chlorins 19 and 21 were synthesised from tripyrrolic nickel complex rac-17 and pyrrole building blocks 12 and 16. The pyrroles are annelated with norbornane moieties which contain the chiral information as well as two different functionalities. The functional groups, namely a carboxylic acid ester and a carbonitrile group, of chlorin 21 finally allowed the formation of an amino acid functionality at the periphery of the macrotetracycle. By using principles of peptide chemistry, the two chlorin subunits were joined to form the peptide-linked chlorin-chlorin dyad 24, which mimics the molecular parts of the natural photosynthetic reaction centre.
Könekamp
Thorsten
T
Institut für Organische Chemie, Universität Bremen, Leobener Strasse NW2/C, 28359 Bremen, Germany.
Ruiz
Anna
A
Duwenhorst
Jörn
J
Schmidt
Wolfgang
W
Borrmann
Tobias
T
Stohrer
Wolf-Dieter
WD
Montforts
Franz-Peter
FP
D008954:Models, Biological; D010455:Peptides / Q000138:chemical synthesis*; D045322:Photosynthetic Reaction Center Complex Proteins / Q000502:physiology*; D011166:Porphyrins / Q000138:chemical synthesis*
D010455:Peptides; D045322:Photosynthetic Reaction Center Complex Proteins; D011166:Porphyrins; C006969:chlorin