title: Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms.
abstract: Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and α-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.
authors: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw 01-224, Poland.
authors: Filip
authors: F
authors: Ulatowski
authors: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw 01-224, Poland.
authors: Janusz
authors: J
authors: Jurczak
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002264:Carboxylic Acids; D013890:Thiourea