Advances in the evaluation of the stability and characteristics of the amino acid and amine derivatives obtained with the o-phthaldialdehyde/3-mercaptopropionic acid and o-phthaldialdehyde/N-acetyl-l-cysteine reagents

Mengerink, Ynze; Kutlán, D; Tóth, Ferenc; Csámpai, Antal; Molnár-Perl, I.

doi:10.1016/s0021-9673(01)01282-1

Cited by 86 publications

(47 citation statements)

References 13 publications

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“…There has been some discrepancy in the literature about the stability of OPA/sulfhydryl substituted amino acids. A rapid decrease of fluorescence intensity described for Gly and Lys derivatives [37] has recently been attributed to the transformation of kinetically formed mono-substituted derivatives into a thermodynamically stable di-substituted derivative [38,39]. Isoindoles that carry an N-CH 2 -R group such as Gly (NH 2 -CH 2 -COOH), ␤-Ala (NH 2 -(CH 2 ) 2 -COOH), GABA (NH 2 -(CH 2 ) 3 -COOH), Lys (NH 2 -(CH 2 ) 4 CHNH 2 -COOH), are especially prone to form adducts that contain both an isoindole and a benzofuran moiety [38,39].…”

Section: Chromatographic Separation Of Amino Acids Derivatized With Omentioning

confidence: 99%

Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography–electrospray ionization mass spectrometry

Hess

Gustafson

Milanowski

et al. 2004

Journal of Chromatography A

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Unusual amino acids such as beta-methoxytyrosine (beta-MeOTyr), allo-threonine (allo-Thr) and allo-isoleucine (allo-Ile) were derivatized with N-alpha-(2,4-dinitro-5-fluorophenyl)-L-alaninamide (FDAA), 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC), (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester (S-NIFE), or o-phthalaldehyde/isobutyryl-L-cysteine (OPA-IBLC), and then separated via reversed-phase high-performance chromatography followed by UV and electrospray ionization mass spectrometry detection. FDAA generally showed the highest enantioselectivity but the lowest sensitivity among the chiral derivatizing agents (CDAs) investigated. The detection limit of FDAA-derivatized amino acids was in the low picomolar range. Although the enantioselectivity of FDAA derivatives was generally quite high, its selectivity among beta-MeOTyr isomers was poor. The best separation of beta-MeOTyr stereoisomers was achieved with S-NIFE. Due to the complex relationships between the investigated CDAs, stereochemical analyses using a combination of two or more of the CDAs gave the most reliable results for a given separation problem. In general, the methods described are selective and reliable, and are being applied to the analysis of unusual amino acids as they occur in marine peptides.

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Section: Chromatographic Separation Of Amino Acids Derivatized With Omentioning

confidence: 99%

Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography–electrospray ionization mass spectrometry

Hess

Gustafson

Milanowski

et al. 2004

Journal of Chromatography A

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“…Recently, the combination of HPLC-FD with ESI-MS has been used to analyze amino acids and amine standards after o-phthaldialdehyde/N-acetyl-L-cysteine (OPA/NAC) derivatization Mengerink et al 2002;Hanczkó et al 2004;Gyimesi-Forrás et al 2005). For this study, we have for the first time combined traditional HPLC-FD with atmospheric ESI-ToF-MS for the identification of OPA/NAC amino acid derivatives in meteorite extracts by fluorescence retention time and exact mass simultaneously.…”

Section: Introductionmentioning

confidence: 99%

Amino acid analyses of Antarctic CM2 meteorites using liquid chromatography-time of flight-mass spectrometry

Glavin

Dworkin

Aubrey

et al. 2006

Meteoritics &Amp; Planetary Science

185

291

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Abstract-Amino acid analyses of the Antarctic CM2 chondrites Allan Hills (ALH) 83100 and Lewis Cliff (LEW) 90500 using liquid chromatography-time of flight-mass spectrometry (LC-ToF-MS) coupled with UV fluorescence detection revealed that these carbonaceous meteorites contain a suite of indigenous amino acids not present in Antarctic ice. Several amino acids were detected in ALH 83100, including glycine, alanine, β-alanine, γ-amino-n-butyric acid (γ-ABA), and α-aminoisobutyric acid (AIB) with concentrations ranging from 250 to 340 parts per billion (ppb). In contrast to ALH 83100, the CM2 meteorites LEW 90500 and Murchison had a much higher total abundance of these amino acids (440-3200 ppb). In addition, ALH 83100 was found to have lower abundances of the α-dialkyl amino acids AIB and isovaline than LEW 90500 and Murchison. There are three possible explanations for the depleted amino acid content in ALH 83100: 1) amino acid leaching from ALH 83100 during exposure to Antarctic ice meltwater, 2) a higher degree of aqueous alteration on the ALH 83100 parent body, or 3) ALH 83100 originated on a chemically distinct parent body from the other two CM2 meteorites. The high relative abundance of ε-amino-n-caproic acid (EACA) in the ALH 83100 meteorite as well as the Antarctic ice indicates that Nylon-6 contamination from the Antarctic sample storage bags may have occurred during collection.

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“…On the other hand, o-phthalaldehyde (OPA) [12][13][14] and naphthalene-2,3-dicarboxaldehyde (NDA) [15][16][17] have been widely used as fluorescence reagents for the derivatization of amino acids and primary amino compounds in the presence of nucleophilic reagent, such as thiol and CN − . Recently, Rammouz et al [18] have given an in-depth review on the use of NDA for the analysis of primary amines in HPLC and CE.…”

Section: Introductionmentioning

confidence: 99%

Fast determination of glutathione by capillary electrophoresis with fluorescence detection using β-cyclodextrin as modifier

Zhang

Sun

2009

Journal of Chromatography B

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Advances in the evaluation of the stability and characteristics of the amino acid and amine derivatives obtained with the o-phthaldialdehyde/3-mercaptopropionic acid and o-phthaldialdehyde/N-acetyl-l-cysteine reagents

Cited by 86 publications

References 13 publications

Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography–electrospray ionization mass spectrometry

Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography–electrospray ionization mass spectrometry

Amino acid analyses of Antarctic CM2 meteorites using liquid chromatography-time of flight-mass spectrometry

Fast determination of glutathione by capillary electrophoresis with fluorescence detection using β-cyclodextrin as modifier

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