Resolution of α-substituted amino acid enantiomers by high-performance liquid chromatography after derivatization with a chiral adduct of o-phthalaldehyde

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

“…A sensitive system for d ‐ and l ‐amino acid analysis was achieved with the use of another early‐developed derivatizing agent, OPA (Maurs et al ., ; Brückner et al ., ). This compound consists of thiol groups and forms with primary amino acids a highly fluorescent derivative.…”

“…A precolumn derivatization by o ‐phthaldialdehyde and N ‐acetyl‐ l ‐cysteine (OPA‐AcCys) reagent was efficient for HPLC resolution of α ‐substituted amino acids (e.g. glutamic acid analogs) on the conventional column Nucleosil 5 (C 18 ) by means of the mobile phase: 0.1 m phosphate buffer containing methanol and fluorometric detection (Maurs et al ., ). Automated pre‐column derivatizatized with OPA and with chiral thiol N ‐isobutyryl‐ l ‐cysteine was applied for chromatographic separation and detection of d ‐ and l ‐amino acids in antibiotic peptides such as bacitracin, gramicidinis A and S, polymyxin B and metanicin C, and also in peptide toxin (malformic).…”

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

“…A sensitive system for d ‐ and l ‐amino acid analysis was achieved with the use of another early‐developed derivatizing agent, OPA (Maurs et al ., ; Brückner et al ., ). This compound consists of thiol groups and forms with primary amino acids a highly fluorescent derivative.…”

“…A precolumn derivatization by o ‐phthaldialdehyde and N ‐acetyl‐ l ‐cysteine (OPA‐AcCys) reagent was efficient for HPLC resolution of α ‐substituted amino acids (e.g. glutamic acid analogs) on the conventional column Nucleosil 5 (C 18 ) by means of the mobile phase: 0.1 m phosphate buffer containing methanol and fluorometric detection (Maurs et al ., ). Automated pre‐column derivatizatized with OPA and with chiral thiol N ‐isobutyryl‐ l ‐cysteine was applied for chromatographic separation and detection of d ‐ and l ‐amino acids in antibiotic peptides such as bacitracin, gramicidinis A and S, polymyxin B and metanicin C, and also in peptide toxin (malformic).…”

HPLC enantioseparation of phenylalanine analogs by application of (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester as a new chiral derivatizing agent

“…OPA-N-acetylcysteine (NAC) derivatization was applied by Florance et al [26] for resolution of the enantiomers of ~-Me-Trp, and by Duchateau et al [27] for the separation ofracemic ~-Me-Val, ~-Me-Leu, ~-Me-Phe, ~-EtPhe and ~-Me-~-Ph-Gly (the abbreviations are in accordance with the IUPAC-IUB-JCBN recommendations [28]). Maurs et al [29] found that most of the ~-Me-amino acids investigated were unresolved or only slightly resolved under these conditions, except for racemic ~-Me-Glu. Duchateau et al [30] applied OPA-D-3-mercapto-2-methylpropionic acid derivatives for the enantioresolution of s-MeVal, ~-Me-Leu, ~-Me-Phe, ~-Me-~-PhGly and ~-Ph-Gly.…”

Effect of various analogues of D-glutamic acid on the D-glutamate-adding enzyme fromEscherichis coli

“…The cyclic analogues of Dglutamic acid were synthesized according to Trigalo et al [7], Modified syntheses and/or separation of the stereoisomers of 2-methyl- [8], 3methyl- [9], 4-methyl- [10,11] and 4-methyleneglutamates [12] will be described elsewhere. Cross-contamination of diastereoisomeric or enantiomeric compounds was about 2-3% as determined by gas-chromatography [13] or HPLC [14]. oL-Phosphinothricin [OL-2-amino-4-(hydroxymethylphosphinyl)butanoic acid] was a generous gift from Hoechst Pflanzenschutzforschung-Biologie (Frankfurt, FRG).…”

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

“…A sensitive system for d ‐ and l ‐amino acid analysis was achieved with the use of another early‐developed derivatizing agent, OPA (Maurs et al ., ; Brückner et al ., ). This compound consists of thiol groups and forms with primary amino acids a highly fluorescent derivative.…”

“…A precolumn derivatization by o ‐phthaldialdehyde and N ‐acetyl‐ l ‐cysteine (OPA‐AcCys) reagent was efficient for HPLC resolution of α ‐substituted amino acids (e.g. glutamic acid analogs) on the conventional column Nucleosil 5 (C 18 ) by means of the mobile phase: 0.1 m phosphate buffer containing methanol and fluorometric detection (Maurs et al ., ). Automated pre‐column derivatizatized with OPA and with chiral thiol N ‐isobutyryl‐ l ‐cysteine was applied for chromatographic separation and detection of d ‐ and l ‐amino acids in antibiotic peptides such as bacitracin, gramicidinis A and S, polymyxin B and metanicin C, and also in peptide toxin (malformic).…”

HPLC enantioseparation of phenylalanine analogs by application of (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester as a new chiral derivatizing agent

“…OPA-N-acetylcysteine (NAC) derivatization was applied by Florance et al [26] for resolution of the enantiomers of ~-Me-Trp, and by Duchateau et al [27] for the separation ofracemic ~-Me-Val, ~-Me-Leu, ~-Me-Phe, ~-EtPhe and ~-Me-~-Ph-Gly (the abbreviations are in accordance with the IUPAC-IUB-JCBN recommendations [28]). Maurs et al [29] found that most of the ~-Me-amino acids investigated were unresolved or only slightly resolved under these conditions, except for racemic ~-Me-Glu. Duchateau et al [30] applied OPA-D-3-mercapto-2-methylpropionic acid derivatives for the enantioresolution of s-MeVal, ~-Me-Leu, ~-Me-Phe, ~-Me-~-PhGly and ~-Ph-Gly.…”

Effect of various analogues of D-glutamic acid on the D-glutamate-adding enzyme fromEscherichis coli

“…The cyclic analogues of Dglutamic acid were synthesized according to Trigalo et al [7], Modified syntheses and/or separation of the stereoisomers of 2-methyl- [8], 3methyl- [9], 4-methyl- [10,11] and 4-methyleneglutamates [12] will be described elsewhere. Cross-contamination of diastereoisomeric or enantiomeric compounds was about 2-3% as determined by gas-chromatography [13] or HPLC [14]. oL-Phosphinothricin [OL-2-amino-4-(hydroxymethylphosphinyl)butanoic acid] was a generous gift from Hoechst Pflanzenschutzforschung-Biologie (Frankfurt, FRG).…”

Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

“…A sensitive system for d ‐ and l ‐amino acid analysis was achieved with the use of another early‐developed derivatizing agent, OPA (Maurs et al ., ; Brückner et al ., ). This compound consists of thiol groups and forms with primary amino acids a highly fluorescent derivative.…”

“…A precolumn derivatization by o ‐phthaldialdehyde and N ‐acetyl‐ l ‐cysteine (OPA‐AcCys) reagent was efficient for HPLC resolution of α ‐substituted amino acids (e.g. glutamic acid analogs) on the conventional column Nucleosil 5 (C 18 ) by means of the mobile phase: 0.1 m phosphate buffer containing methanol and fluorometric detection (Maurs et al ., ). Automated pre‐column derivatizatized with OPA and with chiral thiol N ‐isobutyryl‐ l ‐cysteine was applied for chromatographic separation and detection of d ‐ and l ‐amino acids in antibiotic peptides such as bacitracin, gramicidinis A and S, polymyxin B and metanicin C, and also in peptide toxin (malformic).…”

HPLC enantioseparation of phenylalanine analogs by application of (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester as a new chiral derivatizing agent

“…OPA-N-acetylcysteine (NAC) derivatization was applied by Florance et al [26] for resolution of the enantiomers of ~-Me-Trp, and by Duchateau et al [27] for the separation ofracemic ~-Me-Val, ~-Me-Leu, ~-Me-Phe, ~-EtPhe and ~-Me-~-Ph-Gly (the abbreviations are in accordance with the IUPAC-IUB-JCBN recommendations [28]). Maurs et al [29] found that most of the ~-Me-amino acids investigated were unresolved or only slightly resolved under these conditions, except for racemic ~-Me-Glu. Duchateau et al [30] applied OPA-D-3-mercapto-2-methylpropionic acid derivatives for the enantioresolution of s-MeVal, ~-Me-Leu, ~-Me-Phe, ~-Me-~-PhGly and ~-Ph-Gly.…”

Effect of various analogues of D-glutamic acid on the D-glutamate-adding enzyme fromEscherichis coli

“…The cyclic analogues of Dglutamic acid were synthesized according to Trigalo et al [7], Modified syntheses and/or separation of the stereoisomers of 2-methyl- [8], 3methyl- [9], 4-methyl- [10,11] and 4-methyleneglutamates [12] will be described elsewhere. Cross-contamination of diastereoisomeric or enantiomeric compounds was about 2-3% as determined by gas-chromatography [13] or HPLC [14]. oL-Phosphinothricin [OL-2-amino-4-(hydroxymethylphosphinyl)butanoic acid] was a generous gift from Hoechst Pflanzenschutzforschung-Biologie (Frankfurt, FRG).…”