Crystal Structure and Conformation of a 10-Thiabilirubin |
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Authors: | Adrianne K Tipton David A Lightner |
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Institution: | (1) Department of Chemistry, University of Nevada, Reno, NV 89557-0020, USA, US |
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Abstract: | Summary. A crystal structure determination of a bilirubin analog with a sulfur instead of a C(10)–CH2 linking the two dipyrrinones is reported. Conformation-determining torsion angles and key hydrogen bond distances and angles
are compared to those obtained from molecular dynamics calculations as well as to the corresponding data from X-ray determinations
and molecular dynamics calculations of bilirubin. Like other bilirubins, the component dipyrrinones of the analog are present
in the bis-lactam form with (Z)-configurated double bonds at C(4) and C(15). Despite the large differences in bond lengths and angles at –S–vs.–CH2–, the crystal structure shows considerable similarity to bilirubin: both pigments adopt a folded, intramolecularly hydrogen-bonded
ridge-tile conformation stabilized by six hydrogen bonds – although the interplanar angle of the ridge-tile conformation of
the title compound is smaller (∼ 86°) than that of bilirubin (∼ 98°). The collective data indicate that even with long C–S
bond lengths and a smaller C–S–C bond angle at the pivot point on the ridge-tile seam, intramolecular hydrogen bonding persists.
Received August 16, 2001. Accepted September 12, 2001 |
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Keywords: | , ,Bile pigments, Stereochemistry, Hydrogen bonding, |
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