Synthesis and conformation of a bilirubin analog with propionic acid side chains extended to Undecanoic acid (cas 112-37-8)
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Add time:08/29/2019 Source:sciencedirect.com
A lipophilic analog of bilirubin with propionic acid groups replaced by undecanoic acid groups (1), was synthesized from 11-bromo-undecanoic acid. UV-visible and NMR spectroscopic analyses suggest reduced intramolecular H-bonding and a preference for a helical conformation. Molecular dynamics computations predict a global energy minimum for a helical porphyrin-like conformation with unusual distorted structures when H-bonding is invoked. Circular dichroism of the pigment complex with human serum albumin gives a bilirubin-like bisignate Cotton effect: Δϵmax449 = +33, Δϵmax396 = −47.
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