Péter A, Tóth G, Török G, Tourwé D
Department of Inorganic and Analytical Chemistry, József Attila University, Szeged, Hungary.
J Chromatogr A. 1996 Mar 29;728(1-2):455-65. doi: 10.1016/0021-9673(95)01022-x.
Erythro-D,L- and threo-D,L-beta-methylphenylalanine, -beta-methyltyrosine and -beta-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 beta-methyl amino acids, with the application of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide and 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate as derivatizing reagents. These amino acids were incorporated into the mu-agonist/delta-antagonist opioid peptides H-beta-MeTyr-Tic-Phe-Phe-NH2, H-Tyr-Tic-beta-MePhe-Phe-NH2 and H-Tyr-Tic-Phe-beta-MePhe-NH2, and the delta-antagonist H-Tyr-beta-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.
合成了赤藓糖型-D,L-和苏阿糖型-D,L-β-甲基苯丙氨酸、-β-甲基酪氨酸以及-β-甲基-1,2,3,4-四氢异喹啉-3-羧酸。开发了高效液相色谱法，以1-氟-2,4-二硝基苯基-5-L-丙氨酸酰胺和2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基异硫氰酸酯作为衍生试剂，用于分离和鉴定β-甲基氨基酸的对映体。通过固相肽合成将这些氨基酸引入μ-激动剂/δ-拮抗剂阿片样肽H-β-MeTyr-Tic-Phe-Phe-NH2、H-Tyr-Tic-β-MePhe-Phe-NH2和H-Tyr-Tic-Phe-β-MePhe-NH2以及δ-拮抗剂H-Tyr-β-MeTic-Phe-Phe-OH中。每个肽都有四种立体异构体。肽立体异构体在不同的色谱柱和不同的洗脱系统中进行分离，并确定了肽差向异构体的洗脱顺序。
