Reversed-phase high performance liquid chromatographic separation of diastereomers of beta-amino alcohols and microwave assisted synthesis of Marfey's reagent, its chiral variants and diastereomers.
Ten chiral derivatizing reagents (CDRs) were synthesized by replacing the L-Ala-NH(2) moiety in Marfey's reagent (MR) by seven L-amino acid amides and three L-amino acids employing microwave irradiation (MW) and were characterized. Ten racemic amino alcohols were derivatized with these CDRs under MW. The diastereomers were separated on a reversed-phase C(18) column using binary mixtures of acetonitrile with aqueous trifluoroacetic acid (TFA) and triethylammonium phosphate buffer (TEAP). In general, amino acid variants of MR provided better separation of diastereomers in comparison to amino acid amide variants. The method was also found successful for the separation of 20 diastereomers from a mixture.
Bhushan
Ravi
R
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, India. rbushfcy@iitr.ernet.in
Kumar
Rajender
R
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000605:Amino Alcohols / Q000032:analysis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004136:Dinitrobenzenes / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D016014:Linear Models; D008872:Microwaves; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
D000605:Amino Alcohols; D004136:Dinitrobenzenes; C047134:Marfey's reagent; D000409:Alanine