Stereospecific binding of triostin a to nucleic acid purine base derivatives

Abstract

Triostin A exists as two symmetrical conformers in weakly polar solvents like chloroform. Adenine and guanine derivatives were found to specifically interact with one of the two conformers, but uracil and cytosine derivatives did not. From the analysis of nmr and infrared spectra, it was concluded that the purine derivatives form cyclic hydrogen bonds with the alanine residue of triostin A in addition to the stacking interaction between the purine base and the quinoxaline ring.