797818-01-0Relevant articles and documents
Purine Unit as a Building Block of Artificial Receptors Designed for the Recognition of Carbohydrates
Kaiser, Stefan,Geffert, Christoph,Mazik, Monika
, p. 7555 - 7562 (2019/12/03)
1,3,5-Substituted 2,4,6-triethylbenzene derivatives bearing pyridine/pyrimidine and purine units were synthesized and their potential to function as carbohydrate receptors was evaluated. Compounds consisting of 2-chloro-9H(7H)-purin-6-yl unit have the abi
Highly effective acyclic carbohydrate receptors consisting of aminopyridine, imidazole, and indole recognition units
Mazik, Monika,Kuschel, Matthias
experimental part, p. 2405 - 2419 (2009/04/11)
Neutral imidazole/aminopyridine- and indole/aminopyridine-based receptors, 1 and 2, have been established as highly effective and selective carbohydrate receptors. These receptors effectively recognise neutral carbohydrates through multiple interactions, including neutral hydrogen bonds and CH...π interactions between the sugar CH groups and the aromatic rings of the receptors. The design of these receptors was inspired by the binding motifs observed in the crystal structures of protein-carbohydrate complexes. The formation of very strong complexes with β-glucopyranoside 5, β-maltoside 8, and α-maltoside 9 in organic media has been characterised by 1H NMR spectroscopy and confirmed by a second, independent technique, namely fluorescence spectroscopy. The syntheses, molecular-modelling studies, binding properties of the receptors 1 and 2 toward selected mono- and disaccharides as well as comparative binding studies with receptors 3 and 4 are described.
Molecular recognition of carbohydrates with acyclic pyridine-based receptors
Mazik, Monika,Radunz, Wolfgang,Boese, Roland
, p. 7448 - 7462 (2007/10/03)
The recognition capabilities of acyclic pyridine-based receptors toward monosaccharides were evaluated. Aminopyridine receptors based on the 2,4,6-trimethyl- or 2,4,6-triethylbenzene frame show high β vs α binding selectivity in the recognition of glucopyranosides. Amidopyridine receptors, which are sterically less hindered at nitrogen, display high efficiency and an inverse selectivity. The 2-aminopyridine group has been established as a highly effective recognition group in the binding of monosaccharides. The factors influencing the binding properties of receptors 1-15, which differ in the nature and number of binding and spacer subunits used as the buildings blocks, are discussed.