7613-16-3Relevant articles and documents
Understanding the binding properties of phosphorylated glycoluril-derived molecular tweezers and selective nanomolar binding of natural polyamines in aqueous solution
Heilmann, Michael,Knezevic, Melina,Piccini, Giovannimaria,Tiefenbacher, Konrad
supporting information, p. 3628 - 3633 (2021/05/04)
A modular synthetic platform for the construction of flexible glycoluril-derived molecular tweezers was developed. The binding properties of four exemplary supramolecular hosts obtained via this approach towards 16 organic amines were investigated by means of 1H NMR titration. In this work, we compare the Ka values obtained this way with those of three structurally related molecular tweezers and provide a computational approach towards an explanation of the observed behavior of those novel hosts. The results showcase that certain structural modifications lead to very potent and selective binders of natural polyamines, with observed binding of spermine below 10 nM. This journal is
A Modular Phosphorylated Glycoluril-Derived Molecular Tweezer for Potent Binding of Aliphatic Diamines
Heilmann, Michael,Tiefenbacher, Konrad
supporting information, p. 12900 - 12904 (2019/11/05)
A molecular tweezer based on a glycoluril-derived framework bearing four phosphate groups was synthesized and shown to be capable of binding organic amines in aqueous solution. This work reports the Ka values for 30 complexes of this molecular tweezer and amine guests, determined by means of 1H NMR titrations. Both the hydrophobic cavity and the phosphate groups contribute to the binding. Bulkier molecules and molecules bearing negatively charged groups like carboxylates in amino acids bind less tightly due to a steric clash and coulombic repulsion. The narrow cavity and the strong ionic interactions of the phosphate groups with ammonium guests favor binding of aliphatic diamines. These binding properties clearly distinguish this system from structurally related molecular clips and tweezers.
Synthesis of poly(galactaramides) from alkylene- and substituted alkylenediammonium galactarates
Kiely, Donald E.,Vishwanathan, Arvind,Jarman, Bevan P.,Manley-Harris, Merilyn
experimental part, p. 348 - 368 (2010/01/16)
Polyhydroxypolyamides (PHPAs) represent a class of synthetic polyamides derived from aldaric acid and diamine monomer units. This paper describes the synthesis of some poly(galactaramides), a class of polyhydroxypolyamides, that employs alkylene and subst