DL-Methioninol
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DL-Methioninol

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Category
Amino Alcohol
Catalog number
BAT-002605
CAS number
16720-80-2
Molecular Formula
C5H13NOS
Molecular Weight
135.21
DL-Methioninol
IUPAC Name
2-amino-4-methylsulfanylbutan-1-ol
Alternative CAS
502-83-0
Synonyms
DL-Met-ol; (RS)-2-Amino-4-methylthio-1-butanol; 2-amino-4-(methylthio)butan-1-ol
Appearance
Light yellowish oil
Purity
≥ 99% (HPLC)
Melting Point
31 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C5H13NOS/c1-8-3-2-5(6)4-7/h5,7H,2-4,6H2,1H3
InChI Key
MIQJGZAEWQQAPN-UHFFFAOYSA-N
Canonical SMILES
CSCCC(CO)N
1. Liquid chromatographic enantioseparation of (RS)-mexiletine and (RS)-fluoxetine using chiral derivatizing reagents synthesized with (S)-naproxen moiety
Sonika Batra, Ravi Bhushan Biomed Chromatogr. 2014 Jun;28(6):815-25. doi: 10.1002/bmc.3144.
Enantiomeric separation of racemic mexiletine and fluoxetine was achieved using three chiral derivatizing reagents (CDRs) based on (S)-naproxen. Diastereomers were synthesized by reaction of mexiletine or fluoxetine with the CDRs and were separated on a C18 column under reversed-phase conditions using a binary mixture of acetonitrile and triethylammonium phosphate/water, with UV detection at 230 and 226 nm. The results obtained for enantioseparation of the two drugs using the three CDRs were compiled and compared. The conditions for derivatization and chromatographic separation were optimized. The method was validated for linearity, repeatability, limit of detection and limit of quantification.
2. Indirect enantioseparation of selenomethionine by reversed-phase high-performance liquid chromatography using a newly synthesized chiral derivatizing reagent based on (S)-naproxen moiety
Ravi Bhushan, Hariom Nagar Biomed Chromatogr. 2014 Jan;28(1):106-11. doi: 10.1002/bmc.2903. Epub 2013 Mar 21.
(S)-Naproxen was reacted with N-hydroxyphthalimide in the presence of coupling reagent dicyclohexylcarbodiimide, and a new chiral derivatizing reagent, phthalimidyl-(S)-naproxen ester, was synthesized. It was characterized and was used for synthesis of diastereomers of selenomethionine via microwave irradiation or vortexing. The reaction conditions were optimized. Diastereomeric pairs synthesized by two approaches were successfully separated by reversed-phase high-performance liquid chromatography using binary mixtures of aqueous triethylammonium phosphate and acetonitrile. Detection was carried out at 231 nm. The limit of detection was found to be 0.11 and 0.10 pmol/mL for diastereomers of d- and l-SeMet, respectively. The method was validated for accuracy, precision and limit of detection. The new chiral derivatizing reagent was capable of enantioseparation of dl-SeMet in the form of diastereomers having higher stability, enhanced resolution and lower limits of detection in comparison to the diastereomers prepared with other chiral derivatizing reagents reported in the literature. Optimized structures of the two diastereomers were drawn using the Gaussian 09 Rev. A.02 program and hybrid density functional B3LYP with 6-31G basis set to explain the separation mechanism.
3. Indirect enantioseparation of proteinogenic amino acids using naproxen-based chiral derivatizing reagent and HPLC
Ravi Bhushan, Hariom Nagar Biomed Chromatogr. 2013 Jun;27(6):750-6. doi: 10.1002/bmc.2855. Epub 2012 Dec 7.
Diastereomers of 18 proteinogenic amino acids were synthesized under microwave irradiation and by vortexing using (S)-naproxen-benzotriazole as chiral derivatizing reagent. The diastereomers synthesized by two approaches were found to be identical in terms of their characterization and chromatographic data. A linear gradient of triethylammonium phosphate (pH 3.5)-acetonitrile (30-65%, within 35 min) was found to be successful using reversed-phase high-performance liquid chromatography for their separation. Detection was carried out at 231 nm and sharp peaks were obtained. The method was validated for accuracy, precision and limit of detection.
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