Tetrahedron: Asymmetry

Enantioselection in bilirubin analogs with only one propionic acid group

SE Boiadjiev, DA Lightner

Index: Boiadjiev, Stefan E.; Lightner, David A. Tetrahedron Asymmetry, 1997 , vol. 8, # 21 p. 3603 - 3615

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Citation Number: 9

Abstract

Enantiopure synthetic bilirubin analogs (1 and 2) with only a single β-methyl propionic acid group adopt a folded, ridge-tile conformation stabilized by intramolecular hydrogen bonding. The β-methyl group forces the pigment to adopt a left-handed (M) helical conformation, as evidenced by exciton circular dichroism spectra and indicating that one propionic acid group is sufficient to control the pigment's conformation.