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
[61]   CONSIDERATIONS OF CHIRAL RECOGNITION RELEVANT TO THE LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS [J].
PIRKLE, WH ;
POCHAPSKY, TC .
CHEMICAL REVIEWS, 1989, 89 (02) :347-362
[62]   THIN-LAYER CHROMATOGRAPHIC-SEPARATION OF DIASTEREOMERIC AMINO-ACID DERIVATIVES PREPARED WITH MARFEY REAGENT [J].
RUTERBORIES, KJ ;
NUROK, D .
ANALYTICAL CHEMISTRY, 1987, 59 (22) :2735-2736
[63]   DETERMINATION OF THE CHIRALITY OF AMINO-ACID-RESIDUES IN THE COURSE OF SUBTRACTIVE EDMAN DEGRADATION OF PEPTIDES [J].
SCALONI, A ;
SIMMACO, M ;
BOSSA, F .
ANALYTICAL BIOCHEMISTRY, 1991, 197 (02) :305-310
[64]   D-L AMINO-ACID-ANALYSIS USING AUTOMATED PRECOLUMN DERIVATIZATION WITH 1-FLUORO-2,4-DINITROPHENYL-5-ALANINE AMIDE [J].
SCALONI, A ;
SIMMACO, M ;
BOSSA, F .
AMINO ACIDS, 1995, 8 (03) :305-313
[65]   SEPARATION OF THE DIASTEREOMERS OF BACLOFEN BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY USING CYCLODEXTRIN AS A MOBILE-PHASE ADDITIVE [J].
SHIMADA, K ;
MITAMURA, K ;
MORITA, M ;
HIRAKATA, K .
JOURNAL OF LIQUID CHROMATOGRAPHY, 1993, 16 (15) :3311-3320
[66]   Cysteine Racemization in Peptide Synthesis: A New and Easy Detection Method [J].
Siedler, Frank ;
Weyher, Elisabeth ;
Moroder, Luis .
JOURNAL OF PEPTIDE SCIENCE, 1996, 2 (04) :271-275
[67]  
SOMALI C, 1992, SYNTHESIS-STUTTGART, P285
[68]  
Stevenson D, 1988, CHIRAL SEPARATIONS
[69]   Configuration and racemization determination of cysteine residues in peptides by chiral derivatization and HPLC:: Application to oxytocin peptides [J].
Szabó, S ;
Szókán, G ;
Khlafulla, AM ;
Almás, M ;
Kiss, C ;
Rill, A ;
Schön, I .
JOURNAL OF PEPTIDE SCIENCE, 2001, 7 (06) :316-322
[70]   HPLC enantioseparation of amino acids and their protected derivatives used in peptide synthesis with pre-column chiral derivatization [J].
Szabó, S ;
Khlafulla, R ;
Szarvas, S ;
Almás, M ;
Ladányi, L ;
Szókán, G .
CHROMATOGRAPHIA, 2000, 51 (1) :S193-S201