Abstract
1-fluoro-2,4-dinitrophenyl-5-l-alanine amide has been synthesized in high yield (76%) from 1,5-difluoro-2,4-dinitrobenzene andl-Ala-NH2. This compound contains a reactive fluorine atom which can be used for the reaction with a mixture ofl- andd-amino acids. The resulting diastereomers which are obtained in quantitative yield can be separated and estimated by HPLC. With the five amino acids studied (Ala, Asp, Glu, Met and Phe),l-diastereomers were eluted from the reverse-phase column befored-diastereomers. This behavior can be explained by a stronger intramolecular hydrogen bonding in the latter diastereomer. When artificial mixtures of the five amino acids containing known proportions ofl- andd-isomers were derivatized with the reagent and the reaction products analyzed by HPLC, it was possible to determine the relative content of each isomer in nanomole range.
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Abbreviations
- DMSO:
-
dimethylsulfoxide
- DNDEAP-a a:
-
N-(2,4-dinitro-5-diethylaminophenyl)-amino acid
- DNP:
-
2,4-dinitrophenyl
- FDAA=F-DNP-l-Ala-NH2 :
-
1-fluoro-2,4-dinitrophenyl-5-l-alanine amide
- FFDNB:
-
1,5-difluoro-2,4-dinitrobenzene
- HO-DAA:
-
1-hydroxy-2,4-dinitrophenyl-5-l-alanine amide
- HPLC:
-
high performance liquid chromatography
- l-Ala-NH2-HCl:
-
l-Alanine amide hydrochloride
- TEAP:
-
triethylammonium phosphate
- TLC:
-
thin-layer chromatography
References
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Other abbreviations are according to the guideline of the IUPAC-IUB. Commission of Biochemical Nomenclature.
Accepted by:K. Klenow. E. Lund andS.O. Andersen
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Marfey, P. Determination ofD-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 49, 591 (1984). https://doi.org/10.1007/BF02908688
DOI: https://doi.org/10.1007/BF02908688