Separation of enantiomeric β-methyl amino acids and of β-methyl amino acid containing peptides

A. Péter, Géza Tóth, Gabriella Török, Dirk Tourwé

Research output: Contribution to journalArticle

28 Citations (Scopus)

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 languageEnglish
Pages (from-to)455-465
Number of pages11
JournalJournal of Chromatography A
Volume728
Issue number1-2
DOIs
Publication statusPublished - Mar 29 1996

Fingerprint

phenylalanylphenylalanine
Stereoisomerism
Amino Acids
Peptides
Methyltyrosines
Tics
Solid-Phase Synthesis Techniques
Opioid Peptides
Amides
Alanine
Enantiomers
Liquids
tyrosyl-1,2,3,4--tetrahydroisoquinoline-3-carboxamide
2-tyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

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 journalArticle

Péter, A. ; Tóth, Géza ; Török, Gabriella ; Tourwé, Dirk. / Separation of enantiomeric β-methyl amino acids and of β-methyl amino acid containing peptides. In: Journal of Chromatography A. 1996 ; Vol. 728, No. 1-2. pp. 455-465.
@article{1ad6acc1eb1f46559e6446550282c48d,
title = "Separation of enantiomeric β-methyl amino acids and of β-methyl amino acid containing peptides",
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.",
keywords = "β-methyl, Amino acid, Derivatization, Enantiomer separation, LC, Peptide",
author = "A. P{\'e}ter and G{\'e}za T{\'o}th and Gabriella T{\"o}r{\"o}k and Dirk Tourw{\'e}",
year = "1996",
month = "3",
day = "29",
doi = "10.1016/0021-9673(95)01022-X",
language = "English",
volume = "728",
pages = "455--465",
journal = "Journal of Chromatography",
issn = "0021-9673",
publisher = "Elsevier",
number = "1-2",

}

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 -