title: [The secondary structure of amides of adenylic acid containing D- and L-aromatic amino acids].
abstract: Adenylyl-(5'leads to N)-amino acids containing as amino components, methyl esters of D-, L- and DL-phenylalanine, D-, L- and DL-tyrosine, and D-, L- and DL-tryptophan have been investigated by proton magnetic resonance (PMR) spectroscopy and circular dichroism (CD). The temperature and pD dependences of proton chemical shifts of these compounds have been studied. These data, together with the magnitudes of the upfield chemical shifts of the PMR signals of adenine and aromatic amino acids residues in adenylyl-(5'leads to N)-amino acids, have enabled us to construct conformational models of these compounds. The proposed conformation has been substantiated by the CD results. It is shown that in adenylyl-(5'leads to N)-amino acids the planes of adenine and amino acid aromatic moieties are roughly parallel. The aromatic rings of phenylalanine and tyrosine are localized approximately above the centre of adenine. In adenylyl-(5'leads to N)-D, -(L)-tryptophan, the six-membered rings of the indole overlaps the five-membraned ring of adenine indole partially overlaps the six-membered ring of adenine. A difference in the non-covalent interactions of D- and L-amino acids with nucleotides has been revealed. The mutual localization of the aromatic systems of AMP and the amino acids and also the positions of -OCH3 group with respect to the centre of the amino acid aromatic moiety differs in the series of the studied nucleotide derivatives of D- and L-amino acids.
mesh_terms: D000249:Adenosine Monophosphate; D000577:Amides; D000596:Amino Acids; D002942:Circular Dichroism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008961:Models, Structural; D008968:Molecular Conformation
chemical_list: D000577:Amides; D000596:Amino Acids; D000249:Adenosine Monophosphate
vernacular_title: Osebennosti vtorichnoĭ struktury amidov adenilovoĭ kisloty, soderzhashchikh D- i L-aromaticheskie aminokislety