Marfey's reagent for chiral amino acid analysis:: A review

被引:398
作者
Bhushan, R [1 ]
Brückner, H [1 ]
机构
[1] Univ Giessen, Interdisciplinary Res Ctr, D-35392 Giessen, Germany
关键词
Marfey's reagent (1-fluoro-2,4-dinitrophenyl-5-L-alanine amide, FDAA); pre-column derivatization; enantiomeric resolution; amino acids; proteinogenic; non-proteinogenic; HPLC; chiral variants; separation mechanisms;
D O I
10.1007/s00726-004-0118-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The present paper describes characteristics and application of Marfey's reagent (MR) including general protocols for synthesis of the reagent and diastereomers along with advantages, disadvantages and the required precautions. Applications, and comparison with other derivatizing agents, for the resolution of complex mixtures of DL-amino acids, amines and non-proteinogenic amino acids, peptides/amino acids from microorganisms, cysteine residues in peptides, and evaluation of racemizing characteristics have been discussed. Separation mechanisms of resolution of amino acid diastereomers and replacement of Ala - NH2 by suitable chiral moieties providing structural analogs and different chiral variants and their application as a derivatizing agent to examine the efficiency, and reactivity of the reagent have been focussed. Use of MR for preparing CSPs for direct enantiomeric resolution has also been included.
引用
收藏
页码:231 / 247
页数:17
相关论文
共 77 条
[71]   APPLICATION OF MARFEY REAGENT IN RACEMIZATION STUDIES OF AMINO-ACIDS AND PEPTIDES [J].
SZOKAN, G ;
MEZO, G ;
HUDECZ, F .
JOURNAL OF CHROMATOGRAPHY, 1988, 444 :115-122
[72]  
SZOKAN G, 1989, J LIQ CHROMATOGR, V12, P2855
[73]   HPLC DETERMINATION OF ENANTIOMERIC PURITY OF PROTECTED AMINO-ACID DERIVATIVES USED IN PEPTIDE-SYNTHESIS [J].
SZOKAN, G ;
HADFI, S ;
KRIZSAN, K ;
LIEMBECK, A ;
KRECZ, I ;
ALMAS, M ;
SOMLAI, C .
JOURNAL OF LIQUID CHROMATOGRAPHY, 1994, 17 (13) :2759-2775
[74]   High-performance liquid chromatographic separation of novel atropic α,α-disubstituted-β-amino acids, either on different β-cyclodextrin-bonded phases or as their 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide derivatives [J].
Török, G ;
Péter, A ;
Gaucher, A ;
Wakselman, M ;
Mazaleyrat, JP ;
Armstrong, DW .
JOURNAL OF CHROMATOGRAPHY A, 1999, 846 (1-2) :83-91
[75]   High-performance liquid chromatographic methods for separation of the isomers of β-amino acids possessing bicyclo[2.2.1]heptane or heptene skeletons [J].
Török, G ;
Péter, A ;
Csomós, P ;
Kanerva, LT ;
Fülöp, F .
JOURNAL OF CHROMATOGRAPHY A, 1998, 797 (1-2) :177-186
[76]   FREE SOLUTION CAPILLARY ELECTROPHORESIS AND MICELLAR ELECTROKINETIC RESOLUTION OF AMINO-ACID ENANTIOMERS AND PEPTIDE ISOMERS WITH L-MARFEYS AND D-MARFEYS REAGENTS [J].
TRAN, AD ;
BLANC, T ;
LEOPOLD, EJ .
JOURNAL OF CHROMATOGRAPHY, 1990, 516 (01) :241-249
[77]   Hirsutellide A, a new antimycobacterial cyclohexadepsipeptide from the entomopathogenic fungus Hirsutella kobayasii [J].
Vongvanich, N ;
Kittakoop, P ;
Isaka, M ;
Trakulnaleamsai, S ;
Vimuttipong, S ;
Tanticharoen, M ;
Thebtaranonth, Y .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (09) :1346-1348