title: Validated chiral high performance liquid chromatography separation method and simulation studies of dipeptides on amylose chiral column.
abstract: Chiral resolution of dl-alanine-dl-tyrosine and dl-leucine-dl-phenylalanine dipeptides was achieved on AmyCoat-RP column. The mobile phase used for dl-alanine-dl-tyrosine was acetonitrile-ammonium acetate (10mM, pH 6.0) [50:50, v/v]. It was acetonitrile-methanol-ammonium acetate (10mM; pH adjusted to 4.5 with glacial acetic acid) [50:20:30, v/v] for dl-leucine-dl-phenylalanine. The flow rate of the mobile phases was 0.8mL/min with UV detection at 275nm. The values of retention factors for ll-, dd-, dl- and ld-stereomers of dl-alanine-dl-tyrosine were 1.71, 2.86, 5.43 and 9.42, respectively. The values of separation and resolution factors were 1.67, 1.90 and 1.73 and 2.88, 6.43 and 7.90, respectively. Similarly, these values for dl-leucine-dl-phenylalanine stereomers were 1.50, 2.88, 3.50 and 4.07 (retention factors), 1.92, 1.22 and 1.62 (separation factors) and 2.67, 1.55 and 2.30 (resolution factors). The limits of detections and quantitation were ranged from 2.03 to 6.40 and 6.79 to 21.30μg/mL, respectively. The modeling studies were in agreement with the elution orders. The mechanism of chiral recognition was established by modeling and chromatographic studies. It was observed that hydrogen bondings and π-π interactions are the major forces for chiral separation.
authors.affiliation: Department of Chemistry, Jamia Millia Islamia, (Central University) New Delhi, India. Electronic address: drimran_ali@yahoo.com.
authors.forename: Imran
authors.initials: I
authors.lastname: Ali
authors.affiliation: Department of Chemistry, Jamia Millia Islamia, (Central University) New Delhi, India.
authors.forename: Dibya Ranjan
authors.initials: DR
authors.lastname: Sahoo
authors.affiliation: Department of Chemistry, College of Science, King Saud University, Riyadh 11451, Saudi Arabia.
authors.forename: Zeid A
authors.initials: ZA
authors.lastname: ALOthman
authors.affiliation: Department of Chemistry, College of Science, King Saud University, Riyadh 11451, Saudi Arabia.
authors.forename: Abdulrahman A
authors.initials: AA
authors.lastname: Alwarthan
authors.affiliation: Perm National Research Polytechnic University, Perm, Russia.
authors.forename: Leonid
authors.initials: L
authors.lastname: Asnin
authors.affiliation: Akzo Nobel PPC AB, Separation Products, SE 445 80 Bohus, Sweden.
authors.forename: Bernt
authors.initials: B
authors.lastname: Larsson
mesh_terms: D000688:Amylose / Q000737:chemistry*; D002623:Chemistry Techniques, Analytical / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D003198:Computer Simulation; D004151:Dipeptides / Q000032:analysis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004151:Dipeptides; D000688:Amylose
keywords: AmyCoat-RP; Chiral resolution; Dipeptides; HPLC; Simulation studies