title: Molecular discrimination of N-protected amino acid esters by a self-assembled cylindrical capsule: spectroscopic and computational studies.
abstract: A self-assembled, cylindrical capsule was used to bind N-alpha-protected amino acid esters. The reversible encapsulation was studied using NMR spectroscopy in deuterated mesitylene solution and by computer-aided molecular modeling. BOC-L-alanine alkyl esters and BOC-beta-alanine alkyl esters were tested as guests, and the relative binding affinities were established by direct competition experiments. A good correlation was found between the experimental and calculated relative binding affinities in these two series. Guests that were slightly longer than the internal dimensions of the cavity were accommodated by adopting compacted conformations.
authors.affiliation: The Skaggs Institute for Chemical Biology and The Department of Chemistry, The Scripps Research Institute, MB-26, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Osamu
authors.initials: O
authors.lastname: Hayashida
authors.forename: Lubomir
authors.initials: L
authors.lastname: Sebo
authors.forename: Julius
authors.initials: J
authors.lastname: Rebek
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003198:Computer Simulation; D039301:Computers, Molecular; D004952:Esters / Q000737:chemistry; D046911:Macromolecular Substances; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011487:Protein Conformation
chemical_list: D000596:Amino Acids; D004952:Esters; D046911:Macromolecular Substances; D000409:Alanine