360569-39-7Relevant academic research and scientific papers
Facile synthesis of rotaxanes through condensation reactions of DCC-[2]rotaxanes
Zehnder II, Donald W.,Smithrud, David B.
, p. 2485 - 2487 (2001)
matrix presented In this Letter, we present an easy method for the synthesis of rotaxanes using a novel DCC-[2]rotaxane. The DCC-[2]rotaxane is composed of dibenzo-24-crown-8 ether, an amino acid tether, and di-tert-butyl phenyl rings as blocking groups.
Structure-function relationship of amino acid-[2]rotaxanes
Smukste, Inese,Smithrud, David B.
, p. 2547 - 2558 (2007/10/03)
Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as the ring. A relative measure of the intramolecular interaction energies between the functional groups in DMSO/water mixtures is obtained by comparing their pKa values. Rotaxane structures were investigated through 2D NMR analysis and molecular dynamics simulations. Association constants for complexes of amino acids and rotaxanes in various protonation states were determined in a variety of solvent systems by 1H NMR analysis. The unique intracomponent interactions that exist in the rotaxanes and their ability to act as artificial receptors are discussed.
