Determination ofD-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene
- 1 January 1984
- journal article
- research article
- Published by Springer Science and Business Media LLC in Carlsberg Research Communications
- Vol. 49 (6), 591-596
- https://doi.org/10.1007/bf02908688
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.This publication has 7 references indexed in Scilit:
- New chromogenic reagents for labelling amino groups in peptides. Chromatographic and preparatives aspectsChromatographia, 1981
- Determination of D- and L-Amino Acids by Ion Exchange Chromatography as L-D and L-L DipeptidesJournal of Biological Chemistry, 1968
- [75] Bifunctional reagentsPublished by Elsevier BV ,1967
- REACTION OF BOVINE PANCREATIC RIBONUCLEASE A WITH 1,5-DIFLUORO-2,4-DINITROBENZENE. I. PREPARATION OF MONOMERIC INTRAMOLECULARLY BRIDGED DERIVATIVES.1965
- Reaction of Bovine Pancreatic Ribonuclease A with 1,5-Difluoro-2,4-dinitrobenzenePublished by Elsevier BV ,1965
- Reaction of Bovine Pancreatic Ribonuclease A with 1,5-Difluoro-2,4-dinitrobenzenePublished by Elsevier BV ,1965
- REACTION OF BOVINE PANCREATIC RIBONUCLEASE A WITH 1,5-DIFLUORO-2,4-DINITROBENZENE1965