Conformational Studies of N-2-(3-Indolyl)ethyl- and N-2-Phenylethyl-5'-deoxy-5'-adenosineacetamides by Spectroscopic and Energy Calculation Methods, as Model Compounds for Aminoacyladenylates

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As a part of the conformational studies of aminoacyl adenosine monophosphates, two model compounds, N-2-(3-indolyl)ethyl- and N-2-phenylethyl-5'-deoxy-5'-adenosineacetoamides, were investigated by ultraviolet, circular dichroism and ^1H-nuclear magnetic resonance spectroscopies, and empirical energy calculations. Aromatic ring-ring intramolecular stacking interactions were observed for both compounds. However, the stacking tendency and the ribose puckering accompanying the stacking interaction were different in the two compounds. These conformational differences may be important in the recognition of the tryptophanyl- and phenylalanyladenosine monophosphates by the respective aminoacyladenosine monophosphate synthetases.
1986-05-25