Bilirubin which is now been highlighted as one of the most potent anti-oxidants and is used for combating oxidative stress in various diseases. But in the verve of treatment aspects, we also need to focus on the chemistry of bilirubin. So my prodigious doubt is that whether bilirubin and its derivatives are hybrid compounds?
Dear Rohit,
Yes they are.
A novel conformational structure of bilirubin is presented which obtains maximum
stabilization through a system of four intramolecular hydrogen bonds. Two hydrogen bonds link oxygen and nitrogen atoms of each end ring to the contralateral carboxyl group. 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. In the light of this newly conceived structure the following characteristics of bilirubin are re-evaluated: the stability of the compound, its reaction with diazomethane, the conformational behaviour of its dimethyl ester, its spectral properties, the chirality of the compound when complexed to serum albumin, and the structure of its metal chelates.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1177706/pdf/biochemj00606-0162.pdf
https://www.researchgate.net/publication/18444278_Appendix_Structure_and_conformation_of_bilirubin_Opposing_views_that_invoke_tautomeric_equilibria_hydrogen_bonding_and_a_betaine_may_be_reconciled_by_a_single_resonance_hybrid
Hoping this will be helpful,
Rafik
Article Appendix: Structure and conformation of bilirubin. Opposing ...
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