Structure of bilirubin

@article{Bonnett1976StructureOB,
  title={Structure of bilirubin},
  author={Raymond Bonnett and John E. Davies and Michael B. Hursthouse},
  journal={Nature},
  year={1976},
  volume={262},
  pages={326-328},
  url={https://api.semanticscholar.org/CorpusID:4278361}
}
X-ray analysis of bilirubin is reported—the first such analysis of a naturally occurring linear tetrapyrrole—which shows that bilirUBin has the Z configuration at the C4–C5 and C15–C16 bonds, and possesses in the crystal a ridge tile conformation with considerable intramolecular hydrogen bonding.
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This work reviews research activities on a few of the most relevant structural aspects of bilirubin (BR) and biliverdin (BV) and presents results based on chiroptical spectroscopies, both electronic and vibrational circular dichroism methods, for chirally derivatized BR and BV molecules.

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The isomeric bilirubin dipyrrinone subunits were found to possess important antioxidant activities while being substantially less toxic than bilirube, and the quantum yields of all processes were finding to depend strongly on the wavelength of irradiation, especially when lower energy photons were used.

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15 References

THE ENZYMATIC FORMATION OF BILIRUBIN *

The human organism produces approximately 300 t o 400 mg bilirubin per 24 hr. Approximately 80% of this is derived from hemoglobin of senescent erythrocytes that have been removed from the…

Tautomerism and hydrogen bonding in bilirubin.

The tautomerism ofbilirubin has been the subject of recent investigations (Kuenzle, 1970; Morell, 1969) and we now present additional evidence that the lactam form is the predominant tautomer in…

Bilirubin conjugates of human bile. Nuclear-magnetic-resonance, infrared and optical spectra of model compounds.

N.m.r., i.r. and optical spectra of model compounds were recorded. These were to help in elucidating the structures of the phenylazo derivatives of bilirubin conjugates isolated from human bile.…

Structure and conformation of bilirubin. Opposing views that invoke tautomeric equilibria, hydrogen bonding and a betaine may be reconciled by a single resonance hybrid.

The proposed structure can explain a variety of uncommon features of bilirubin, and reconciles many seemingly contradictory hypotheses by accommodating them in individual structures which are mesomeric forms of one resonance hybrid.

Tautomerism and hydrogen bonding in bilirubin and biliverdin.

Stability of Bilirubin

With aged preparations, a certain amount of insoluble substance is observed which dissolves within a few seconds when boiled under reflux, due to either an isomerization from bilirubin to dihydrobiliverdin—a displacement of the π electrons from the vinyl to the central methylene bridge2—or a transition between two crystalline phases, the less soluble having the highest thermodynamical stability.

Structure of Bilirubin

Compared to the esters, pure bilirubin is relatively stable and reacts with the diazoreagent only when an accelerator is added.

Interactions of bilirubin with bovine serum albumin in aqueous solution.

Crystallographic studies in the pyrrole series. Part II. Crystal and molecular structure of 5,5′-diethoxycarbonyl-3,3′,4,4′-tetraethyldipyrrol-2-ylmethane

Crystals of the title compound (III) are monoclinic, space group P21/c, with cell dimensions a= 8·655(2), b= 17·781(4), c= 15·465(4)A and β= 102·70(2)°. The structure was solved by direct methods and…

Crystallographic studies in the pyrrole series. Part I. Crystal and molecular structure of ethyl 4-acetyl-3-ethyl-5-methylpyrrole-2-carboxylate

Crystals of the title compound are monoclinic, space group P21/n, Z= 4, with cell dimensions a= 6·772(3), b= 14·628(5), c= 12·187(5)A, and β= 94·20(12)°. The structure was solved by direct methods,…