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2 Acta Biochimica Polonica

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Association of model peptides and dehydropeptides: N-acetyl-L-butyrine and [Z]-dehydrobutyrine N',N'-dimethylamides

100%

Broda M. A. , Rzeszotarska B.

tom 53

nr 1

These comparative studies on the aggregation behaviour of Ac-(Z)-ΔAbu-NMe2 and Ac-L-Abu-NMe2 in carbon tetrachloride were performed by the analysis of their FTIR spectra and by theoretical calculations. The percentage of the monomeric form (α) decreased as concentration increased and this occurred to a higher degree for the (Z)-ΔAbu derivative than for its saturated analogue. The dimerization constant KD, calculated on the basis of the intensity of the monomer and associate bands in the νs(N-H) vibration region, is by three orders of magnitude larger for Ac-(Z)-ΔAbu-NMe2 than for Ac-L-Abu-NMe2. The obtained dimer geometries of the dehydro- compound were calculated by the B3LYP/6-31+G** method.

Conformational properties of N',N'-dimethylamides of N-acetyldehydroalanine and N-acetyl-[Z]-dehydrophenylalanine

84%

Siodlak D. , Broda M. A. , Rzeszotarska B. , Koziol A. E. , Dybala I.

Acta Biochimica Polonica

2001

tom 48

nr 4

Conformational preferences of Ac-ΔAla-NMe2 and Ac-(Z)-ΔPhe-NMe2 were studied and compared with those of their monomethyl counterparts as well as with those of their saturated analogues. X-Ray data and energy calculations revealed a highly conservative conformation of the dehydro dimethylamides, which is located in a high-energy region of the Ramachandran map.