title: Enantiomeric separations using polymeric L-glutamate surfactant derivatives: effect of increasing steric factors.
abstract: This study examines the role of steric hindrance near the stereogenic centers of four glutamic acid based polymeric surfactants. The single amino acid surfactants of glutamic acid, glutamic acid methyl ester, glutamic ethyl ester, and glutamic acid tert-butyl ester were investigated. The micellar electrokinetic chromatography (MEKC) separation of three binaphthyl derivatives and three benzodiazepines were used to study these steric factors. In addition, the hydrophobicity of these polymers as a function of pH was investigated by use of fluorescence measurements.
authors.affiliation: Discovery Chemistry Research and Technologies, Lilly Research Laboratories, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, IN, USA.
authors.forename: Stefan J
authors.initials: SJ
authors.lastname: Thibodeaux
authors.forename: Eugene
authors.initials: E
authors.lastname: Billiot
authors.forename: Eric
authors.initials: E
authors.lastname: Torres
authors.forename: Bertha C
authors.initials: BC
authors.lastname: Valle
authors.forename: Isiah M
authors.initials: IM
authors.lastname: Warner
mesh_terms: D001569:Benzodiazepines / Q000737:chemistry / Q000302:isolation & purification*; D001704:Biopolymers / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D018698:Glutamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D001704:Biopolymers; D009281:Naphthalenes; D013501:Surface-Active Agents; D001569:Benzodiazepines; C031721:naphthalene; D018698:Glutamic Acid