Coformational energy calculations on the 1-aminocyclopentane-1-carboxylic acid monopeptide Ac-Acc5-NHMe indicate that this Cα,α-dialkylated, cyclic α-amino acid residue is conformationally restricted and that its minimum energy conformation falls in the α/310-helical region. The results of the theoretical analysis are in agreement with the crystal-state structural tendency of pBrBz(Acc5)4OtBu·2MeOH, pBrBz(Acc5)5OtBu·MeOH, and Z(Acc5)6OtBu, determined by X-ray diffraction and also described in this work (formation of 310-helices). The implications for the use of Acc5 residues in designing conformationally constrained analogues of bioactive peptides are briefly discussed. © 1988.

STRUCTURAL VERSATILITY OF PEPTIDES FROM C-ALPHA,ALPHA-DIALKYLATED GLYCINES - A CONFORMATIONAL ENERGY CALCULATION AND X-RAY-DIFFRACTION STUDY OF HOMOPEPTIDES FROM 1-AMINOCYCLOPENTANE-1-CARBOXYLIC ACID

BARONE, Vincenzo;
1988

Abstract

Coformational energy calculations on the 1-aminocyclopentane-1-carboxylic acid monopeptide Ac-Acc5-NHMe indicate that this Cα,α-dialkylated, cyclic α-amino acid residue is conformationally restricted and that its minimum energy conformation falls in the α/310-helical region. The results of the theoretical analysis are in agreement with the crystal-state structural tendency of pBrBz(Acc5)4OtBu·2MeOH, pBrBz(Acc5)5OtBu·MeOH, and Z(Acc5)6OtBu, determined by X-ray diffraction and also described in this work (formation of 310-helices). The implications for the use of Acc5 residues in designing conformationally constrained analogues of bioactive peptides are briefly discussed. © 1988.
1988
1-Aminocyclopentane-1-carboxylic acid (Acc; 5; ) peptides; conformational energy; helices; X-ray diffraction;
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11384/12001
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