Homorubins and Homoverdins.
Monatsh Chem
; 145(6): 963-981, 2014 Jun.
Article
en En
| MEDLINE
| ID: mdl-25110360
ABSTRACT
The syntheses are described for centrally expanded bilirubin analogs b -homorubins with propionic and butyric acid groups in the positions corresponding to the propionic acids of bilirubin. Their syntheses were accomplished by coupling two equivalents of a reactive monopyrrole (5-(bromomethylene)pyrrolin-2-one) to a dipyrrylethane. The corresponding b -homoverdins and dehydro- b -homoverdins were prepared by dehydrogenating the rubins or their dimethyl esters using DDQ. As supported by NMR measurements and molecular mechanics calculations, the homorubins are found to engage in conformation-determining intramolecular hydrogen bonding between the dipyrrinone and carboxylic acid moieties. Likewise, the homoverdins are believed to favor intramolecularly hydrogen-bonded conformations.
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01-internacional
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MEDLINE
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En
Revista:
Monatsh Chem
Año:
2014
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Article