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Crystal Structure and Conformation of a 10-Thiabilirubin
Authors:Adrianne K Tipton and David A Lightner
Institution:(1) Departamento de F?sica Fundamental II, Universidad de La Laguna, 38206 La Laguna, Tenerife, Spain;(2) Instituto de Ciencia de Materiales de Arag?n, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza, Spain
Abstract: 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.
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