Abstract:

Ten novel amino acid derived chiral stationary phases(CSPs), including eight amino acid modified triazine derived CSPs(CSP-1~CSP-8) and two N-p-methylbenzoyl L-amino acid CSPs(CSP-9~CSP-10), were prepared from L-valine and L-alanine. The chiral recognition ability of these CSPs was evaluated for regioisomers of o-, m-, p-nitrophenol and six racemates of naproxen ethyl ester, propiconazole, difenoconazole, tebuconazole, hexaconazole, 1,1'-bi-2-naphthol, under normal phase mode. The results show that CSP-1~CSP-3 and CSP-6~CSP-8 exhibit good selectivity for three regioisomers of nitrophenol. The CSPs obtained from L-alanine show better enantioselective recognition toward the racemates, which leads to a baseline separation of naproxen ethyl ester on CSP-6. Meanwhile, the binding mode and association energy of L-alanine three-substituted triazine derivative CSP Ⅵ with R or S naproxen ethyl ester were investigated by computational simulation with Gaussian 09 software, and hydrogen bonding was found to be a significant factor on the enantioselective recognition.

Key words: amino acid derivatives, chiral stationary phases, chiral separation, Gaussian 09