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
Full Text: HTML
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.
Related Articles:
[Woodward, Robert Burns; Ayer, William A.; Beaton, John M.; Bickelhaupt, Friedrich; Bonnett, Raymond; Buchschacher, Paul; Closs, Gerhard L.; Dutler, Hans; Hannah, John; Hauck, Fred P.; Ito, Sho; Langemann, Albert; Le Goff, Eugene; Leimgruber, Willy; Lwowski, Walter; Sauer, Juergen; Valenta, Zdenek; Volz, Heinrich Tetrahedron, 1990 , vol. 46, # 22 p. 7599 - 7659]
[Kleinspehn Journal of the American Chemical Society, 1955 , vol. 77, p. 1546]