Journal
TETRAHEDRON-ASYMMETRY
Volume 14, Issue 9, Pages 1133-1140Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(03)00156-3
Keywords
-
Ask authors/readers for more resources
In a recent work addressing the structural characterization of melanin pigments, we reported the isolation and characterization of trimeric oligomers of 5,6-dihydroxyindole-2-carboxylic acid (DHICA), a key intermediate in the biosynthesis of the dark brown eumelanins, by tyrosine catalyzed oxidation of the indole under biomimetic conditions. These oligomers feature atropisomerism and consequently, we wished to investigate chirality in such systems. Herein, we report two significant steps forward in this study: The isolation of a regiosymmetric DHICA tetramer by means of a model approach involving oxidation of the main DHICA dimer, namely 4,4'-biindolyl and the first resolution of eumelanin intermediates. This also allowed the absolute stereochemistry of the newly isolated tetramer to be defined by applying the exiton chirality method. (C) 2003 Elsevier Science Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available