TY - JOUR
T1 - Demonstration of a common indole-based aromatic core in natural and synthetic eumelanins by solid-state NMR
AU - Chatterjee, Subhasish
AU - Prados-Rosales, Rafael
AU - Tan, Sindy
AU - Itin, Boris
AU - Casadevall, Arturo
AU - Stark, Ruth E.
PY - 2014/9/14
Y1 - 2014/9/14
N2 - Despite the essential functions of melanin pigments in diverse organisms and their roles in inspiring designed nanomaterials for electron transport and drug delivery, the structural frameworks of the natural materials and their biomimetic analogs remain poorly understood. To overcome the investigative challenges posed by these insoluble heterogeneous pigments, we have used l-tyrosine or dopamine enriched with stable 13C and 15N isotopes to label eumelanins metabolically in cell-free and Cryptococcus neoformans cell systems and to define their molecular structures and supramolecular architectures. Using high-field two-dimensional solid-state nuclear magnetic resonance (NMR), our study directly evaluates the assumption of structural commonality between synthetic melanin models and the corresponding natural pigments, demonstrating a common indole-based aromatic core in the products from contrasting synthetic protocols for the first time. This journal is
AB - Despite the essential functions of melanin pigments in diverse organisms and their roles in inspiring designed nanomaterials for electron transport and drug delivery, the structural frameworks of the natural materials and their biomimetic analogs remain poorly understood. To overcome the investigative challenges posed by these insoluble heterogeneous pigments, we have used l-tyrosine or dopamine enriched with stable 13C and 15N isotopes to label eumelanins metabolically in cell-free and Cryptococcus neoformans cell systems and to define their molecular structures and supramolecular architectures. Using high-field two-dimensional solid-state nuclear magnetic resonance (NMR), our study directly evaluates the assumption of structural commonality between synthetic melanin models and the corresponding natural pigments, demonstrating a common indole-based aromatic core in the products from contrasting synthetic protocols for the first time. This journal is
UR - http://www.scopus.com/inward/record.url?scp=84905757854&partnerID=8YFLogxK
U2 - 10.1039/c4ob01066c
DO - 10.1039/c4ob01066c
M3 - Article
C2 - 25047903
AN - SCOPUS:84905757854
SN - 1477-0520
VL - 12
SP - 6730
EP - 6736
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 34
ER -