Enantioseparation and thermodynamic study ...
Document type :
Article dans une revue scientifique
DOI :
PMID :
Permalink :
Title :
Enantioseparation and thermodynamic study of naphthalene derivatives, new melatoninergic agonists, on coated amylose [tris(S)-1phenylethylcarbamate] stationary phase. Transposition to preparative scale
Author(s) :
Landagaray, Elodie [Auteur]
Yous, Said [Auteur]
Lille Neurosciences & Cognition (LilNCog) - U 1172
Vaccher, Claude [Auteur]
Lipka, Emmanuelle [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Lille Inflammation Research International Center - U 995 [LIRIC]
Lille Inflammation Research International Center (LIRIC) - U995
Yous, Said [Auteur]

Lille Neurosciences & Cognition (LilNCog) - U 1172
Vaccher, Claude [Auteur]

Lipka, Emmanuelle [Auteur]

Lille Inflammation Research International Center - U 995 [LIRIC]
Lille Inflammation Research International Center - U 995 [LIRIC]
Lille Inflammation Research International Center (LIRIC) - U995
Journal title :
Biomedical chromatography . BMC
Abbreviated title :
Biomed. Chromatogr.
Volume number :
29
Pages :
689-697
Publication date :
2015-05-01
ISSN :
0269-3879
English keyword(s) :
Van''t Hoff linearization
chirality
naphthalene
polysaccharide stationary phase
preparative separation
thermodynamic parameters
chirality
naphthalene
polysaccharide stationary phase
preparative separation
thermodynamic parameters
HAL domain(s) :
Sciences du Vivant [q-bio]
English abstract : [en]
This work reports a high-performance liquid chromatography normal-phase methodology to elucidate enantiomers of naphthalene derivatives, evaluated as melatoninergic agonists. For this purpose four different polysaccharide ...
Show more >This work reports a high-performance liquid chromatography normal-phase methodology to elucidate enantiomers of naphthalene derivatives, evaluated as melatoninergic agonists. For this purpose four different polysaccharide based chiral stationary phases were evaluated, namely Chiralcel OD-H (cellulose tris-3,5-dimethylphenylcarbamate), Chiralcel OJ (cellulose tris-methylbenzoate), Chiralpak AD (amylose tris-3,5-dimethylphenylcarbamate) and Chiralpak AS (amylose tris-(S)-1-phenylethylcarbamate) with different alcoholic modifiers on different amounts in n-heptane. A temperature study was carried out, between 20 and 40 °C and the apparent thermodynamic parameters were calculated thanks to the Van't Hoff linearization. For all compounds (except 3), ΔΔH° and ΔΔS° exhibited positive values ranging from 791.2 to 9999.3 J/mol and from 3.9 to 37.8 J/K/mol respectively, indicating entropically driven separations. Optimized conditions led to goof resolution of 2.37 for compound 1 on Chiralpak AS, with heptane-2-propanol 90:10 (v/v), at a temperature of 30 °C. Then they were transposed to the preparative scale for compound 1, generating 22 mg of each enantiomer with an 80% yield. The limits of detection and of quantification were determined to allow the calculation of the enantiomeric excess. They were found with very low values, equal to 0.32 and 1.05 µ m and 0.33 and 1.11 µ m, respectively, for peaks 1 and 2 of compound 1.Show less >
Show more >This work reports a high-performance liquid chromatography normal-phase methodology to elucidate enantiomers of naphthalene derivatives, evaluated as melatoninergic agonists. For this purpose four different polysaccharide based chiral stationary phases were evaluated, namely Chiralcel OD-H (cellulose tris-3,5-dimethylphenylcarbamate), Chiralcel OJ (cellulose tris-methylbenzoate), Chiralpak AD (amylose tris-3,5-dimethylphenylcarbamate) and Chiralpak AS (amylose tris-(S)-1-phenylethylcarbamate) with different alcoholic modifiers on different amounts in n-heptane. A temperature study was carried out, between 20 and 40 °C and the apparent thermodynamic parameters were calculated thanks to the Van't Hoff linearization. For all compounds (except 3), ΔΔH° and ΔΔS° exhibited positive values ranging from 791.2 to 9999.3 J/mol and from 3.9 to 37.8 J/K/mol respectively, indicating entropically driven separations. Optimized conditions led to goof resolution of 2.37 for compound 1 on Chiralpak AS, with heptane-2-propanol 90:10 (v/v), at a temperature of 30 °C. Then they were transposed to the preparative scale for compound 1, generating 22 mg of each enantiomer with an 80% yield. The limits of detection and of quantification were determined to allow the calculation of the enantiomeric excess. They were found with very low values, equal to 0.32 and 1.05 µ m and 0.33 and 1.11 µ m, respectively, for peaks 1 and 2 of compound 1.Show less >
Language :
Anglais
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
Université de Lille
CHU Lille
Inserm
CHU Lille
Inserm
Collections :
Submission date :
2019-02-26T17:11:50Z