(R)-N-(3,5-dinitrobenzoyl)-1-naphthylglycine as a chiral stationary phase for the separation of enantiomers by high-performance liquid chromatography

Ôi, Naobumi; Kitahara, Hajimu; Matsumoto, Yu; Nakajima, Hisako O.; Horikawa, Yasuhiko

doi:10.1016/s0021-9673(00)91365-7

Cited by 34 publications

(8 citation statements)

References 7 publications

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“…In the first dimension, the fractions of NBD-Ser and NBD-Ala were collected as their D plus L mixtures by a capillary monolithic-ODS column, and the enantiomers were further separated by a narrowbore enantioselective column in the second dimension. As an enantioselective column, a Pirkle-type column (Sumichiral OA-2500S, [17,18]) was used. In the rat plasma, trace amounts of D-Ser and D-Ala were clearly determined without severe interference by intrinsic compounds in the tissues.…”

Section: Enantioselective 2d-hplc Analysis Of Ser and Ala In Mammalsmentioning

confidence: 99%

Enantioselective Two-Dimensional High-Performance Liquid Chromatographic Determination of Amino Acids; Analysis and Physiological Significance of D-Amino Acids in Mammals

et al. 2014

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D-Amino acids are now increasingly recognized as physiologically functional molecules and biomarkers in mammals. However, the amounts of D-amino acids are extremely low in most cases, thus highly sensitive and selective analytical methods are practically essential. In the present review article, enantioselective two-dimensional high-performance liquid chromatographic (2D-HPLC) methods are introduced and their applications to the determination of D-amino acids in mammalian samples are described. For the sensitive determination, amino acid enantiomers are derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F), and are determined by a fluorescence detector. The 2D-HPLC system consists of the reversed-phase non-enantioselective, but chemoselective separation of NBD-amino acids in the first dimension, and the sequential chiral separation in the second dimension. By using the system, neuroactive D-amino acids (D-Ser and D-Ala) were determined in the brain of various mammalian species and the regulation of their intrinsic amounts are also demonstrated. The physiological and diagnostic meanings of the trace amounts of D-Ser are also discussed. The 2D-HPLC systems for the acidic D-amino acids (D-Asp and D-Glu), proline analogues (D-Pro, trans-and cis-4-hydroxy-D-Pro) and hydrophilic D-amino acids (D-Arg, D-Asn, D-Asp, D-Gln, D-Glu, D-His, D-Ser, D-allo-Thr and D-Thr) are also shown.

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Section: Enantioselective 2d-hplc Analysis Of Ser and Ala In Mammalsmentioning

confidence: 99%

Enantioselective Two-Dimensional High-Performance Liquid Chromatographic Determination of Amino Acids; Analysis and Physiological Significance of D-Amino Acids in Mammals

et al. 2014

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“…The amount of d-Asp was around 1000 nmol/g tissue, and was higher than that of l-Asp in the tissue. In the study, the amino acids were derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F [28]), and the enantiomers were separated using a Pirkletype chiral stationary phase, Sumichiral OA-2500S [29]. By using this enantioselective column, the selective determination of NBD-Asp enantiomers could be performed.…”

Section: Determination Of D-amino Acids In Mammals Using Chiral Statimentioning

confidence: 99%

HPLC analysis of naturally occurring free d-amino acids in mammals

Miyoshi

Koga

Oyama

et al. 2012

Journal of Pharmaceutical and Biomedical Analysis

106

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“…The commercial availability of several ionically bonded CSPs prompted a necessity to explore similar linkages with oligoproline selector [21,31]. Ionically bonded diproline CSPs with single tether (CSP4) and double tethers (CSP3) were easily prepared by acid -base reactions on the functionalized silica gel [20].…”

Section: Ionically Bonded Diproline Cspsmentioning

confidence: 99%

“…Several ionically bonded brush-type CSPs have been developed and shown good chromatographic results [20,21]. Since linker of oligoproline CSPs significantly affects their chiral recognition ability, it is necessary to investigate more connection manners, e.g., ionically bonding, on oligoproline CSPs.…”

Section: Introductionmentioning

confidence: 99%

Doubly tethered tertiary amide linked and ionically bonded diproline chiral stationary phases

Lao

Gan

2009

J of Separation Science

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Oligoproline chiral stationary phase (CSP) is a new class peptide chiral stationary phase. Many proline chiral stationary phases with different proline chain lengths and linkers have been prepared and evaluated. However, the doubly tethered and ionic type linkers have not been adequately investigated. In this study, covalently and ionically bonded chiral stationary phases with doubly tethered linker were prepared and characterized. The new covalently bonded doubly tethered diproline CSP was applied successfully to resolve various enantiomers of acidic, basic, and neutral compounds with phenyl, naphthyl, anthryl, or similarly sized groups. The enantiorecognition performances of singly and doubly tethered diproline CSPs were comparable. Variation of the type and content of organic modifiers in hexane or heptane mobile phase showed that the branch alcohols such as 2-propanol and 2-butanol, 1,2-dichloroethane, methyl tert-butyl ether, and ethyl acetate in the mobile phase enhanced chiral separation. End-capping on doubly tethered diproline CSP did not always improve the separation factor and resolution. Due to the rigid structure of the double tether, the enantioseparation ability of ionically bonded diproline CSP was well expressed to some analytes.

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(R)-N-(3,5-dinitrobenzoyl)-1-naphthylglycine as a chiral stationary phase for the separation of enantiomers by high-performance liquid chromatography

Cited by 34 publications

References 7 publications

Enantioselective Two-Dimensional High-Performance Liquid Chromatographic Determination of Amino Acids; Analysis and Physiological Significance of D-Amino Acids in Mammals

Enantioselective Two-Dimensional High-Performance Liquid Chromatographic Determination of Amino Acids; Analysis and Physiological Significance of D-Amino Acids in Mammals

HPLC analysis of naturally occurring free d-amino acids in mammals

Doubly tethered tertiary amide linked and ionically bonded diproline chiral stationary phases

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