Abstract
Optically active bilirubin analogs ( 1 and 2) with a stereogenic center in each propionic acid side chain were synthesized and examined by CD and NMR spectroscopy. Introduction of an α-methyl and a β-methyl forces the pigment to adopt either a left-handed ( M) or right-handed ( P) helicity with a folded, ridge-tile conformation. As evidenced by exciton-type circular dichroism spectra, the ( αS,α′S- 3 ), ( βS,β′S- 5 ), ( αS,β′S- 1 ) stereoisomers strongly prefer the M- helicity ridge-tile conformation, but the ( αR, β′ S) stereoisomer ( 2) prefers the P- helicity .
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