title: Binding of carboxylate and trimethylammonium salts to octa-acid and TEMOA deep-cavity cavitands.
abstract: In participation of the fifth statistical assessment of modeling of proteins and ligands (SAMPL5), the strength of association of six guests (3-8) to two hosts (1 and 2) were measured by1H NMR and ITC. Each host possessed a unique and well-defined binding pocket, whilst the wide array of amphiphilic guests possessed binding moieties that included: a terminal alkyne, nitro-arene, alkyl halide and cyano-arene groups. Solubilizing head groups for the guests included both positively charged trimethylammonium and negatively charged carboxylate functionality. Measured association constants (Ka) covered five orders of magnitude, ranging from 56 M-1for guest 6 binding with host 2 up to 7.43 × 106M-1for guest 6 binding to host 1.
authors.affiliation: Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Sullivan
authors.affiliation: Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.
authors.forename: Punidha
authors.initials: P
authors.lastname: Sokkalingam
authors.affiliation: Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.
authors.forename: Thong
authors.initials: T
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.
authors.forename: James P
authors.initials: JP
authors.lastname: Donahue
authors.affiliation: Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA. bgibb@tulane.edu.
authors.forename: Bruce C
authors.identifier: 0000-0002-4478-4084
authors.initials: BC
authors.lastname: Gibb
mesh_terms: D001665:Binding Sites; D002264:Carboxylic Acids / Q000737:chemistry*; D015195:Drug Design; D008024:Ligands; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011485:Protein Binding; D011506:Proteins / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D050337:Trimethyl Ammonium Compounds / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D008024:Ligands; D047028:Macrocyclic Compounds; D011506:Proteins; D050337:Trimethyl Ammonium Compounds
keywords: Cavitand; Host-guest chemistry; Hydrophobic effect