Application of amino acid amides as chiral auxiliaries in difluoro dinitro benzene and cyanuric chloride moieties for high-performance liquid-chromatographic enantioseparation of selenomethionine and its mixture with methionine and cysteine |
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Authors: | Bhushan Ravi Dubey Rituraj |
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Institution: | (1) Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667, India |
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Abstract: | l-Ala-NH2, l-Val-NH2, l-Leu-NH2, and d-Phg-NH2 were used as chiral auxiliaries to synthesize four chiral derivatizing reagents (CDRs) of each of the three categories, viz.,
difluoro dinitro benzene (DFDNB) based chiral variants, and cyanuric chloride (CC) based monochloro-s-triazine reagents (MCTs)
and dichloro-s-triazine reagents (DCTs). DFDNB based chiral variants were synthesized by substituting one of the fluorine
atoms of DFDNB with respective amino acid amides. The MCTs and DCTs were synthesized by substituting chlorine atom with aforesaid
amino acid amide moieties in 6-methoxy dichloro-s-triazine and in CC, respectively. In total, 12 CDRs were characterized and
used for microwave-assisted synthesis (45 s at 80% of 800 W using DFDNB-based chiral variants, 80 s at 90% of 800 W power
using MCTs, and 50 s at 80% of 800 W power using DCTs) of diastereomers of (A) SeMet, and (B) mixture of (1) SeMet and Met,
and (2) SeMet, Met, and Cys. The diastereomers were enantioseparated by reversed-phase high-performance liquid chromatography
using gradient elution with mobile phases containing aq. TFA (0.1%)—MeCN in different compositions. The method was validated
for accuracy, precision, and limit of detection. |
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