Tetrahedron

Synthesis and conformation of a bilirubin analog with propionic acid side chains extended to undecanoic acid

J Chiefari, RV Person, DA Lightner

Index: Chiefari, John; Person, Richard V.; Lightner, David A. Tetrahedron, 1992 , vol. 48, # 29 p. 5969 - 5984

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Citation Number: 8

Abstract

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 ...