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Synthesis of a Peptide‐Linked Chlorin Dyad as a Model Compound for the Photosynthetic Reaction Centre
Author(s) -
Könekamp Thorsten,
Ruiz Anna,
Duwenhorst Jörn,
Schmidt Wolfgang,
Borrmann Tobias,
Stohrer WolfDieter,
Montforts FranzPeter
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700222
Subject(s) - chlorin , pyrrole , chemistry , peptide , photosynthetic reaction centre , stereochemistry , dyad , combinatorial chemistry , photosynthesis , organic chemistry , porphyrin , biochemistry , psychology , social psychology
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.