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: High-performance liquid chromatography-mass spectrometry study

Y. Mengerink, D. Kutlán, F. Tóth, A. Csámpai, I. Molnár-Perl

Research output: Contribution to journalArticle

76 Citations (Scopus)

Abstract

The composition of the amino acid and amine derivatives obtained with the o-phthaldialdehyde (OPA)/3-mercaptopropionic acid (MPA) and with the OPA/N-acetyl-L-cysteine (NAC) reagents was investigated by on-line HPLC-electrospray ionization MS. The initially formed derivatives proved to be, as expected, the corresponding isoindoles while their transformed species contained one additional OPA molecule. Based on the MS spectra of all transformed OPA derivatives a reaction pathway is suggested. This reaction mechanism was supported both by the molecular ions of the endproducts and by the presence of several selective fragment ions that served as an explanation to the structure of the believed to be less stable OPA derivatives. It has been shown that more than one OPA derivative forms in all those cases when the compound to be derivatized does contain the NH2-CH2-R moiety. Thus, amino acids like e.g. glycine, histidine, β-alanine, γ-aminobutyric acid, ε-aminocaproic acid, ornithine, and also several aliphatic mono- and diamines provide more than one OPA derivative. Analytical consequences of this experience were utilized by altering the reagent's composition. Reagents containing mole ratios of [OPA]/[MPA] or [OPA]/[NAC]=1/50 resulted in two benefits, simultaneously: (i) in a decrease of the transformation rate of the initially formed derivative, and, (ii) in an increase of the overall stability of the total of derivatives.

Original languageEnglish
Pages (from-to)99-124
Number of pages26
JournalJournal of Chromatography A
Volume949
Issue number1-2
DOIs
Publication statusPublished - Mar 8 2002

Fingerprint

3-Mercaptopropionic Acid
o-Phthalaldehyde
Acetylcysteine
High performance liquid chromatography
Amines
Mass spectrometry
Mass Spectrometry
High Pressure Liquid Chromatography
Derivatives
Amino Acids
Isoindoles
Ions
Aminobutyrates
Aminocaproic Acid
Electrospray ionization
Ornithine
Diamines
Chemical analysis
Histidine
Alanine

Keywords

  • Acetylcysteine
  • Amines
  • Amino acids
  • Derivatization, LC
  • Mercaptopropionic acid
  • Phthaldialdehyde

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

@article{fce8840f570945f99375075f62bac44e,
title = "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: High-performance liquid chromatography-mass spectrometry study",
abstract = "The composition of the amino acid and amine derivatives obtained with the o-phthaldialdehyde (OPA)/3-mercaptopropionic acid (MPA) and with the OPA/N-acetyl-L-cysteine (NAC) reagents was investigated by on-line HPLC-electrospray ionization MS. The initially formed derivatives proved to be, as expected, the corresponding isoindoles while their transformed species contained one additional OPA molecule. Based on the MS spectra of all transformed OPA derivatives a reaction pathway is suggested. This reaction mechanism was supported both by the molecular ions of the endproducts and by the presence of several selective fragment ions that served as an explanation to the structure of the believed to be less stable OPA derivatives. It has been shown that more than one OPA derivative forms in all those cases when the compound to be derivatized does contain the NH2-CH2-R moiety. Thus, amino acids like e.g. glycine, histidine, β-alanine, γ-aminobutyric acid, ε-aminocaproic acid, ornithine, and also several aliphatic mono- and diamines provide more than one OPA derivative. Analytical consequences of this experience were utilized by altering the reagent's composition. Reagents containing mole ratios of [OPA]/[MPA] or [OPA]/[NAC]=1/50 resulted in two benefits, simultaneously: (i) in a decrease of the transformation rate of the initially formed derivative, and, (ii) in an increase of the overall stability of the total of derivatives.",
keywords = "Acetylcysteine, Amines, Amino acids, Derivatization, LC, Mercaptopropionic acid, Phthaldialdehyde",
author = "Y. Mengerink and D. Kutl{\'a}n and F. T{\'o}th and A. Cs{\'a}mpai and I. Moln{\'a}r-Perl",
year = "2002",
month = "3",
day = "8",
doi = "10.1016/S0021-9673(01)01282-1",
language = "English",
volume = "949",
pages = "99--124",
journal = "Journal of Chromatography",
issn = "0021-9673",
publisher = "Elsevier",
number = "1-2",

}

TY - JOUR

T1 - 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

T2 - High-performance liquid chromatography-mass spectrometry study

AU - Mengerink, Y.

AU - Kutlán, D.

AU - Tóth, F.

AU - Csámpai, A.

AU - Molnár-Perl, I.

PY - 2002/3/8

Y1 - 2002/3/8

N2 - The composition of the amino acid and amine derivatives obtained with the o-phthaldialdehyde (OPA)/3-mercaptopropionic acid (MPA) and with the OPA/N-acetyl-L-cysteine (NAC) reagents was investigated by on-line HPLC-electrospray ionization MS. The initially formed derivatives proved to be, as expected, the corresponding isoindoles while their transformed species contained one additional OPA molecule. Based on the MS spectra of all transformed OPA derivatives a reaction pathway is suggested. This reaction mechanism was supported both by the molecular ions of the endproducts and by the presence of several selective fragment ions that served as an explanation to the structure of the believed to be less stable OPA derivatives. It has been shown that more than one OPA derivative forms in all those cases when the compound to be derivatized does contain the NH2-CH2-R moiety. Thus, amino acids like e.g. glycine, histidine, β-alanine, γ-aminobutyric acid, ε-aminocaproic acid, ornithine, and also several aliphatic mono- and diamines provide more than one OPA derivative. Analytical consequences of this experience were utilized by altering the reagent's composition. Reagents containing mole ratios of [OPA]/[MPA] or [OPA]/[NAC]=1/50 resulted in two benefits, simultaneously: (i) in a decrease of the transformation rate of the initially formed derivative, and, (ii) in an increase of the overall stability of the total of derivatives.

AB - The composition of the amino acid and amine derivatives obtained with the o-phthaldialdehyde (OPA)/3-mercaptopropionic acid (MPA) and with the OPA/N-acetyl-L-cysteine (NAC) reagents was investigated by on-line HPLC-electrospray ionization MS. The initially formed derivatives proved to be, as expected, the corresponding isoindoles while their transformed species contained one additional OPA molecule. Based on the MS spectra of all transformed OPA derivatives a reaction pathway is suggested. This reaction mechanism was supported both by the molecular ions of the endproducts and by the presence of several selective fragment ions that served as an explanation to the structure of the believed to be less stable OPA derivatives. It has been shown that more than one OPA derivative forms in all those cases when the compound to be derivatized does contain the NH2-CH2-R moiety. Thus, amino acids like e.g. glycine, histidine, β-alanine, γ-aminobutyric acid, ε-aminocaproic acid, ornithine, and also several aliphatic mono- and diamines provide more than one OPA derivative. Analytical consequences of this experience were utilized by altering the reagent's composition. Reagents containing mole ratios of [OPA]/[MPA] or [OPA]/[NAC]=1/50 resulted in two benefits, simultaneously: (i) in a decrease of the transformation rate of the initially formed derivative, and, (ii) in an increase of the overall stability of the total of derivatives.

KW - Acetylcysteine

KW - Amines

KW - Amino acids

KW - Derivatization, LC

KW - Mercaptopropionic acid

KW - Phthaldialdehyde

UR - http://www.scopus.com/inward/record.url?scp=0037040606&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037040606&partnerID=8YFLogxK

U2 - 10.1016/S0021-9673(01)01282-1

DO - 10.1016/S0021-9673(01)01282-1

M3 - Article

C2 - 11999763

AN - SCOPUS:0037040606

VL - 949

SP - 99

EP - 124

JO - Journal of Chromatography

JF - Journal of Chromatography

SN - 0021-9673

IS - 1-2

ER -