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- W1946148923 abstract "The 1H NMR spectra of the L, L and D, L diastereomers of the protected linear dipeptides Boc- (and Tfa)-Ala-N(Me)Ala-OMe, Boc- (and Tfa)-Phe-N(Me)Ala-OMe, Z-Ala-(Λ-thia)Pec-OMe and Z-Phe-(Λ-thia)Pec-OMe (Pec = pipecolic acid) have been recorded in chloroform, dimethylsulfoxide and benzene at room temperature. The observed side chain vicinal coupling constants and ring current effects indicated a conformational preference of the Phe side chain for the “extended-to-oxygen” rotamer (X1 torsion angle of 180°) in the cis isomer (ω= 0°) of the L, L- and in the trans isomer (ω= 180°) of the D, L-dipeptides. Concomitantly, these L, L-cis and D, L-trans isomers were more populated in the Phe-Xxx as compared to the Ala-Xxx sequences (Xxx = the imino acid). The results are explained in terms of an attractive interaction between the aromatic ring and the succeeding amide bond." @default.
- W1946148923 created "2016-06-24" @default.
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- W1946148923 date "2009-01-12" @default.
- W1946148923 modified "2023-09-25" @default.
- W1946148923 title "Aromatic side chain rotational preference" @default.
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- W1946148923 doi "https://doi.org/10.1111/j.1399-3011.1986.tb03297.x" @default.
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