Separation of amino acid and peptide stereoisomers by nonionic micelle-mediated capillary electrophoresis after chiral derivatization

Enantiomers of amino acids and peptides were derivatized with a fluorescent chiral reagent, 4-(3-isothiocyanatopyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole [ R-(−)- or S-(+)-NBD-PyNCS] and the resulting diastereomeric derivatives separated by capillary electrophoresis (CE). The CE running buffer co...

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Bibliographic Details
Published in:	Journal of Chromatography A Vol. 800; no. 2; pp. 345 - 354
Main Authors:	Liu, Yi-Ming, Schneider, Michael, Sticha, Cheryl M., Toyooka, Toshimasa, Sweedler, Jonathan V.
Format:	Journal Article
Language:	English
Published:	Amsterdam Elsevier B.V 27-03-1998 Elsevier
Subjects:	Amino acids Amino Acids - analysis Amino Acids - chemistry Aminoacids, peptides. Hormones. Neuropeptides Analytical chemistry Analytical, structural and metabolic biochemistry Animals Anti-Bacterial Agents - analysis Anti-Bacterial Agents - chemistry Biological and medical sciences Chemistry Chromatographic methods and physical methods associated with chromatography Electrophoresis, Capillary - methods Exact sciences and technology Fluorescent Dyes - chemistry Fundamental and applied biological sciences. Psychology Gramicidin - analysis Gramicidin - chemistry Immune Sera - immunology Isothiocyanates - chemistry Micelles Other chromatographic methods Oxadiazoles - chemistry Peptides Proteins Rabbits Stereoisomerism Derivatization, electrophoresis Amino acids Peptides Micelles Enantiomer separation Biological fluid Separation Aplysia californica Micellar electrokinetic capillary chromatography Rabbit Surfactant polymer Gastropoda Derivatization Biological material Blood Ethylene oxide polymer Gramicidin Enantiomer Fluorescence detector Capillary electrophoresis Non ionic surfactant Laser induced fluorescence Lagomorpha α-Aminoacid Vertebrata Antibiotic Mammalia Optical resolution Fluorescent labelling Animal Buccal ganglion Invertebrata Mollusca Blood serum
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Summary:	Enantiomers of amino acids and peptides were derivatized with a fluorescent chiral reagent, 4-(3-isothiocyanatopyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole [ R-(−)- or S-(+)-NBD-PyNCS] and the resulting diastereomeric derivatives separated by capillary electrophoresis (CE). The CE running buffer consisted of 25 m M acetate buffer (pH 4) and 10 m M of the nonionic surfactant Triton X-100. The excitation maximum of NBD-PyNCS at 480 nm matches the major Ar-ion emission line at 488 nm allowing sensitive laser-induced fluorescence detection with limits of detection around 50 n M. d-Proline and d-aspartate spiked (at 10 −4 M and 10 −5 M concentrations, respectively) into complex biological matrices (rabbit serum and homogenate of Aplysia californica buccal ganglion) are detected without matrix interferences. This method has also been applied to the determination of d- and l-amino acid residues in peptides after acid hydrolysis. Results from the chiral analysis of the naturally-occurring peptide, gramicidin D, are shown.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0021-9673
DOI:	10.1016/S0021-9673(97)01137-0