Abstract
Biliverdin oligopeptides have been prepared with the aim of complete chiral discrimination of the conformationally labile bilatriene helix. Evidence is given that appropriately constituted biliverdin–tripeptides and -tetrapeptides exhibit diastereoisomeric homogenity in solution. To ascertain the homochirality of the bilatriene helices present in a bilipeptide two independent approaches were used: invariability of the chiroptical properties towards (i) successive peptide chain lengthening and towards (ii) the polarity of the solvent. The c.d. parameters of the inherently chiral bilatriene (P)-helix are thus evaluated to be ΔIµ+ 100 to + 110 and ΔIµ–130 to –150 for the red and blue band, respectively. These parameters belong to a bilatriene helix whose torsional angles closely resemble those of biliverdin dimethyl ester.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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