A novel stopped-flow multidimensional HPLC (sf-MD-HPLC) procedure has been developed to investigate simultaneously the effect of the pH on the enantiostability and hydrolysis of (±)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide [(±)IDRA21]. It was possible to determinate the rate constants and free energy barriers of enantiomerization and hydrolysis rate constants of (±)IDRA21, by using two chiral stationary phases (CSPs) and one achiral C18 column. A classical batchwise kinetic method was used to calculate rate constants of hydrolysis at the same temperature and in the same buffers used in sf-MD-HPLC. The good agreement of the results obtained validate the sf-MD-HPLC procedure. Furthermore, hydrolysis rate constants of (±)IDRA21 were calculated in a series of buffers over a pH range of 1.20-10.60 at 37 °C in order to evaluate the influence of the pH on hydrolysis.

Enantiomerization and hydrolysis of (±)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide by stopped-flow multidimensional high-performance liquid chromatography / Cannazza, Giuseppe; Carrozzo, Marina Maria; Braghiroli, Daniela; Parenti, Carlo. - In: JOURNAL OF CHROMATOGRAPHY A. - ISSN 0021-9673. - STAMPA. - 1212(2008), pp. 41-47. [10.1016/j.chroma.2008.09.087]

Enantiomerization and hydrolysis of (±)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide by stopped-flow multidimensional high-performance liquid chromatography

CANNAZZA, Giuseppe;CARROZZO, Marina Maria;BRAGHIROLI, Daniela;PARENTI, Carlo
2008

Abstract

A novel stopped-flow multidimensional HPLC (sf-MD-HPLC) procedure has been developed to investigate simultaneously the effect of the pH on the enantiostability and hydrolysis of (±)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide [(±)IDRA21]. It was possible to determinate the rate constants and free energy barriers of enantiomerization and hydrolysis rate constants of (±)IDRA21, by using two chiral stationary phases (CSPs) and one achiral C18 column. A classical batchwise kinetic method was used to calculate rate constants of hydrolysis at the same temperature and in the same buffers used in sf-MD-HPLC. The good agreement of the results obtained validate the sf-MD-HPLC procedure. Furthermore, hydrolysis rate constants of (±)IDRA21 were calculated in a series of buffers over a pH range of 1.20-10.60 at 37 °C in order to evaluate the influence of the pH on hydrolysis.
1212
41
47
Enantiomerization and hydrolysis of (±)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide by stopped-flow multidimensional high-performance liquid chromatography / Cannazza, Giuseppe; Carrozzo, Marina Maria; Braghiroli, Daniela; Parenti, Carlo. - In: JOURNAL OF CHROMATOGRAPHY A. - ISSN 0021-9673. - STAMPA. - 1212(2008), pp. 41-47. [10.1016/j.chroma.2008.09.087]
Cannazza, Giuseppe; Carrozzo, Marina Maria; Braghiroli, Daniela; Parenti, Carlo
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11380/860230
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