DERIVATIZATION OF DL-AMINO ACIDS BY URETHANE-PROTECTED ALPHA-AMINO-ACID N-CARBOXYANHYDRIDES FOR SEPARATION BY LC

被引:11
作者
BRUCKNER, H
LUPKE, M
机构
[1] Institute of Food Technology, University of Hohenheim, Stuttgart
关键词
COLUMN LIQUID CHROMATOGRAPHY; AMINO ACID ANALYSIS; CHIRALITY; DIASTEREOISOMERS; DIPEPTIDES;
D O I
10.1007/BF02290275
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Using a robotic autosampler, free DL-amino acids were derivatized with highly reactive, urethane-protected, L-alpha-amino acid N-carboxyanhydrides (NCAs) with structures: Boc-Phe-NCA, Boc-Asn(Trt)-NCA, Fmoc-Lys(Boc)-NCA, Fmoc-Met-NCA, Fmoc-Ala-NCA, Z-Ala-NCA, Z-Val-NCA and Z-Leu-NCA (Boc = tert-butyloxycarbonyl, Trt = trityl, Fmoc = 9-(fluor-enyl-methyl)oxycarbonyl, Z = benzyloxycarbonyl). Using sodium berate buffer and acetonitrile solvent, derivatization was complete in 3.5 min at room temperature. By selection of an appropriate reagent, the resulting diastereomeric, N-protected dipeptides were separated on an octylsilica stationary phase using mixtures of sodium acetate buffer and acetonitrile as eluents.
引用
收藏
页码:601 / 606
页数:6
相关论文
共 33 条
[1]  
AHNOFF M, 1989, CHIRAL LIQUID CHROMA, P39
[3]   Z-GLN(TRT)-AIB-AIB-AIB-OME SYNTHESIS USING UNCA AND BOP PYBROP COUPLING METHODS [J].
AUVINGUETTE, C ;
FREROT, E ;
COSTE, J ;
REBUFFAT, S ;
JOUIN, P ;
BODO, B .
TETRAHEDRON LETTERS, 1993, 34 (15) :2481-2482
[4]  
BENOITON NL, 1988, INT J PEPT PROT RES, V31, P581
[5]   HPLC SEPARATION OF DL-AMINO ACIDS DERIVATIZED WITH N2-(5-FLUORO-2,4-DINITROPHENYL)-L-AMINO ACID-AMIDES [J].
BRUCKNER, H ;
KELLERHOEHL, C .
CHROMATOGRAPHIA, 1990, 30 (11-12) :621-629
[6]   LIQUID-CHROMATOGRAPHIC DETERMINATION OF D-AMINO AND L-AMINO-ACIDS BY DERIVATIZATION WITH O-PHTHALDIALDEHYDE AND CHIRAL THIOLS [J].
BRUCKNER, H ;
HAASMANN, S ;
LANGER, M ;
WESTHAUSER, T ;
WITTNER, R ;
GODEL, H .
JOURNAL OF CHROMATOGRAPHY A, 1994, 666 (1-2) :259-273
[7]   CHROMATOGRAPHIC DETERMINATION OF D-AMINO ACIDS AS NATIVE CONSTITUENTS OF VEGETABLES AND FRUITS [J].
BRUCKNER, H ;
WESTHAUSER, T .
CHROMATOGRAPHIA, 1994, 39 (7-8) :419-426
[8]   USE OF CHIRAL MONOHALO-S-TRIAZINE REAGENTS FOR THE LIQUID-CHROMATOGRAPHIC RESOLUTION OF DL-AMINO ACIDS [J].
BRUCKNER, H ;
STRECKER, B .
JOURNAL OF CHROMATOGRAPHY, 1992, 627 (1-2) :97-105
[9]   USE OF CHROMOGENIC AND FLUORESCENT OXYCARBONYL CHLORIDES AS REAGENTS FOR AMINO-ACID-ANALYSIS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
BRUCKNER, H ;
LUPKE, M .
JOURNAL OF CHROMATOGRAPHY A, 1995, 697 (1-2) :295-307
[10]   HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC SEPARATION OF DL-AMINO ACIDS DERIVATIZED WITH CHIRAL VARIANTS OF SANGER REAGENT [J].
BRUCKNER, H ;
GAH, C .
JOURNAL OF CHROMATOGRAPHY, 1991, 555 (1-2) :81-95