Self-organizing lariat ether derivatives ordered by hydrogen-bonded and stacked nucleotide bases

Abstract

A novel bibracchial lariat ether based upon 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (A2O3T3A) has been prepared which has CH₂CH₂adenine (2A) and CH₂CH₂CH₂thymineOCH₂CH₂adenine (3T3A) side-arms; the terminal adenine in the 3T3A side-arm folds parallel to and π-stacks with the thymine in the same side-arm while the adenines in opposite side-arms form a single hydrogen bond as judged by two-dimensional NOESY studies.