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Synthesis of a Peptide-Linked Chlorin Dyad as a Model Compound for the Photosynthetic Reaction Centre

✍ Scribed by Thorsten Könekamp; Anna Ruiz; Jörn Duwenhorst; Wolfgang Schmidt; Tobias Borrmann; Wolf-Dieter Stohrer; Franz-Peter Montforts

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 310 KB
Volume: 13
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200700222

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✦ Synopsis

Abstract

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.

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