Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 23, Pages 6595-6604Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200700222
Keywords
chlorin; dyes/pigments; peptide linkages; photosynthesis; porphyrinoids
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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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