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Abstract:
Two cyclic peptide like compounds, cyclo-anthranoyl-L- prolyl (1) and cyclo-homoanthranoyl-L-prolyl (2) have been synthesized and investigated by UV spectroscopy and measurement of circular dichroism. Compound 1 of entirely rigid conformation with two N-CO groups conjugated to the aromatic ring, Ar-NH-CO left handed helical, Ar-CO-N right handed helical, shows a very strong positive Cotton effect centered around 250 nm and a strong negative one centered around 227 nm. Compound 2, which has only one conjugated skewed electron system, Ar-NH-CO, can exist in two different stable conformations, one of them being left handed, the other one right handed helical. It also shows a strong positive Cotton effect centered around 235 nm. Since from earlier 13C NMR data the latter was concluded to be the preferred conformation, a right handed helical sense of the amide bond-aromatic ring system is likely to correlate with a positive Cotton effect of this inherently dissymmetric chromophore.
