6533b852fe1ef96bd12ab538

RESEARCH PRODUCT

Association of model peptides and dehydropeptides: N-acetyl-L-butyrine and (Z)-dehydrobutyrine N',N'-dimethylamides.

Barbara RzeszotarskaMałgorzata A. Broda

subject

chemistry.chemical_classificationHydrogen bondStereochemistryDimerInfrared spectroscopyPeptideGeneral Biochemistry Genetics and Molecular Biologychemistry.chemical_compoundCrystallographyMonomerchemistryCarbon tetrachlorideOrders of magnitude (speed)Derivative (chemistry)

description

These comparative studies on the aggregation behaviour of Ac-(Z)-DeltaAbu-NMe(2) and Ac-L-Abu-NMe(2) in carbon tetrachloride were performed by the analysis of their FTIR spectra and by theoretical calculations. The percentage of the monomeric form (alpha) decreased as concentration increased and this occurred to a higher degree for the (Z)-DeltaAbu derivative than for its saturated analogue. The dimerization constant K(D), calculated on the basis of the intensity of the monomer and associate bands in the nu(s)(N-H) vibration region, is by three orders of magnitude larger for Ac-(Z)-DeltaAbu-NMe(2) than for Ac-L-Abu-NMe(2). The obtained dimer geometries of the dehydro- compound were calculated by the B3LYP/6-31+G** method.

https://doi.org/10.18388/abp.2006_3381