Conformational Features of 5'-O-[N-(L-Alanyl)sulfamoyl]adenosine, a Substrate Analogue of Alanyl-tRNA Synthetase, Studied by ^1H-NMR and Energy Calculation Methods

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The solution conformation of 5'-O-[N-(L-alanyl)sulfamoyl]adenosine (ala-SA), an analogue of alanyl-AMP, was studied by ^1H-NMR spectroscopic and energy calculation methods for elucidating the substrate-specificity of the cognate alanyl-tRNA synthetase. The ala-SA molecule existed in several conformational equilibria such as anti⇌syn, C3'-endo⇌C2'-endo and gauche・gauche⇌gauche・trans (or trans・gauche) orientations concerning the glycosyl bond, ribose puckering and exocyclic C4'-C5' bond, respectively. However, their populations were solvent-dependent, and the major form in D_2O solution could be characterized as the anti-C2'-endo-gauche・gauche conformation, although no predominant conformation, except for C2'-endo ribose puckering, existed in dimethyl sulfoxide solution. Possible conformers satisfying the NMR data were surveyed using empirical energy calculations, and the solution conformation of the ala-SA molecule was compared with its crystal conformation.
社団法人日本薬学会の論文
1993-05-15