Abstract
Erythro-D,L- and threo-D,L-β-methylphenylalanine, -β-methyltyrosine and -β-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid were synthesized. High-performance liquid chromatographic methods were developed for the separation and identification of the enantiomers of the β-methyl amino acids, with the application of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate as derivatizing reagents. These amino acids were incorporated into the μ-agonist/δ-antagonist opioid peptides H-β-MeTyr-Tic-Phe-Phe-NH2, H-Tyr-Tic-β-MePhe-Phe-NH2 and H-Tyr-Tic-Phe-β-MePhe-NH2, and the δ-antagonist H-Tyr-β-MeTic-Phe-Phe-OH, by solid-phase peptide synthesis. Each peptide has four stereoisomers. The peptide stereoisomers were separated on different columns and in different eluent systems and the elution order of the peptide epimers was determined.
| Original language | English |
|---|---|
| Pages (from-to) | 455-465 |
| Number of pages | 11 |
| Journal | Journal of Chromatography A |
| Volume | 728 |
| Issue number | 1-2 |
| DOIs | |
| Publication status | Published - Mar 29 1996 |
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Keywords
- β-methyl
- Amino acid
- Derivatization
- Enantiomer separation
- LC
- Peptide
ASJC Scopus subject areas
- Analytical Chemistry
Cite this
Separation of enantiomeric β-methyl amino acids and of β-methyl amino acid containing peptides. / Péter, A.; Tóth, Géza; Török, Gabriella; Tourwé, Dirk.
In: Journal of Chromatography A, Vol. 728, No. 1-2, 29.03.1996, p. 455-465.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Separation of enantiomeric β-methyl amino acids and of β-methyl amino acid containing peptides
AU - Péter, A.
AU - Tóth, Géza
AU - Török, Gabriella
AU - Tourwé, Dirk
PY - 1996/3/29
Y1 - 1996/3/29
N2 - Erythro-D,L- and threo-D,L-β-methylphenylalanine, -β-methyltyrosine and -β-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid were synthesized. High-performance liquid chromatographic methods were developed for the separation and identification of the enantiomers of the β-methyl amino acids, with the application of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate as derivatizing reagents. These amino acids were incorporated into the μ-agonist/δ-antagonist opioid peptides H-β-MeTyr-Tic-Phe-Phe-NH2, H-Tyr-Tic-β-MePhe-Phe-NH2 and H-Tyr-Tic-Phe-β-MePhe-NH2, and the δ-antagonist H-Tyr-β-MeTic-Phe-Phe-OH, by solid-phase peptide synthesis. Each peptide has four stereoisomers. The peptide stereoisomers were separated on different columns and in different eluent systems and the elution order of the peptide epimers was determined.
AB - Erythro-D,L- and threo-D,L-β-methylphenylalanine, -β-methyltyrosine and -β-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid were synthesized. High-performance liquid chromatographic methods were developed for the separation and identification of the enantiomers of the β-methyl amino acids, with the application of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate as derivatizing reagents. These amino acids were incorporated into the μ-agonist/δ-antagonist opioid peptides H-β-MeTyr-Tic-Phe-Phe-NH2, H-Tyr-Tic-β-MePhe-Phe-NH2 and H-Tyr-Tic-Phe-β-MePhe-NH2, and the δ-antagonist H-Tyr-β-MeTic-Phe-Phe-OH, by solid-phase peptide synthesis. Each peptide has four stereoisomers. The peptide stereoisomers were separated on different columns and in different eluent systems and the elution order of the peptide epimers was determined.
KW - β-methyl
KW - Amino acid
KW - Derivatization
KW - Enantiomer separation
KW - LC
KW - Peptide
UR - http://www.scopus.com/inward/record.url?scp=0039117872&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0039117872&partnerID=8YFLogxK
U2 - 10.1016/0021-9673(95)01022-X
DO - 10.1016/0021-9673(95)01022-X
M3 - Article
C2 - 8673237
AN - SCOPUS:0039117872
VL - 728
SP - 455
EP - 465
JO - Journal of Chromatography
JF - Journal of Chromatography
SN - 0021-9673
IS - 1-2
ER -