title: Direct and indirect separations of five isomers of Brivanib Alaninate using chiral high-performance liquid chromatography.
abstract: Brivanib Alaninate is a novel chiral prodrug possessing two stereogenic centers. Simultaneous HPLC separation of five isomers of Brivanib Alaninate was systematically investigated on a wide variety of polysaccharide-based chiral stationary phases (CSPs) using underivatization and pre-column derivatization methods. The influence of derivatizing groups and mobile phase composition on the enantioseparation and retention behavior of Brivanib Alaninate compounds was studied. To better understand the chiral recognition mechanism, the temperature effect was also evaluated. The results of these studies led to the first complete HPLC resolution of all five isomers of Brivanib Alaninate as carbobenzyloxy (CBZ) derivatives on a cellulose benzoate CSP (OJ-H).
authors.affiliation: Bristol-Myers Squibb Research and Development, New Brunswick, NJ 08903, USA. lingfeng_he@hotmail.com
authors.forename: Brian Lingfeng
authors.initials: BL
authors.lastname: He
authors.forename: Yueer
authors.initials: Y
authors.lastname: Shi
authors.forename: Brent
authors.initials: B
authors.lastname: Kleintop
authors.forename: Thomas
authors.initials: T
authors.lastname: Raglione
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D011134:Polysaccharides / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature; D014227:Triazines / Q000302:isolation & purification*
chemical_list: D011134:Polysaccharides; D014227:Triazines; C509922:brivanib; D000409:Alanine