Abstract
Two new chiral monochloro-s-triazines (MCT) were synthesized [viz N-(4-chloro-6-piperidinyl-[1,3,5]-triazine-2-yl)-l-leucine amide and N-(4-chloro-6-piperidinyl-[1,3,5]-triazine-2-yl)-l-leucine) (CDR 1 and 2, respectively)] by the nucleophilic displacement of chlorine atoms in s-triazine moiety. One of the Cl atoms was replaced with piperidine, and the second Cl atom in the 6-piperidinyl derivative was replaced with amino acid amide (viz l-Leu–NH2) and amino acid (l-Leu). These reagents were characterized and used as CDRs for chiral separation of protein and non-protein amino acids, and were separated on a reversed-phase C18 column. The reaction conditions were optimized for the synthesis of diastereomers using one MCT reagent. The separation method was validated for limit of detection, linearity, accuracy, precision, and recovery.
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Acknowledgments
The authors are thankful to the Ministry of Human Resources Development, Government of India, New Delhi for the award of a research assistantship (to C.A.) and to the Alexander von Humboldt Foundation, Bonn, Germany for donating Knauer HPLC equipment and to the Council of Scientific and Industrial Research, New Delhi, India for financial assistance [to R.B.; research grant No. 01(2334)/09/EMR-II].
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Bhushan, R., Agarwal, C. Reversed-phase liquid chromatographic resolution of diastereomers of protein and non-protein amino acids prepared with newly synthesized chiral derivatizing reagents based on cyanuric chloride. Amino Acids 40, 403–409 (2011). https://doi.org/10.1007/s00726-010-0650-z
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DOI: https://doi.org/10.1007/s00726-010-0650-z