Upon DNP-aromatic rule. Effect of introducing a methyl group to the .BETA.-position upon the CD spectra of DNP derivatives of aromatic .ALPHA.-amino acids.

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CD spectra of N-DNP-O-benzoyl derivatives of L-serine, L-threonine, and L-allothreonine and DNP derivatives of L-phenylalanine and (βR)- and (βS)-β-methyl-L-phenylalanines were studied. The effect of methyl substitution at the β-position upon their CD spectra was explained by the change in the population of the rotamer g− (χ1=−60°) which was shown to be responsible for the characteristic negative Cotton effect at ≈400 nm. The negative sign of the [θ]≈400max values of the DNP derivatives of aromatic L-α-amino acids described by DNP-aromatic rule was proved to be due to the contribution of the rotamer g−.
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