Nα-(2,4-Dinitro-5-fluorophenyl)-L-alanine amide
Need Assistance?
  • US & Canada:
    +
  • UK: +

Nα-(2,4-Dinitro-5-fluorophenyl)-L-alanine amide

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

A derivatizing chiral agent that can be used for detection of underivatized amino acids in HPLC.

Category
Fluorinated Amino Acids
Catalog number
BAT-000444
CAS number
95713-52-3
Molecular Formula
C9H9N4O5F
Molecular Weight
272.20
Nα-(2,4-Dinitro-5-fluorophenyl)-L-alanine amide
IUPAC Name
(2S)-2-(5-fluoro-2,4-dinitroanilino)propanamide
Synonyms
FDNP-L-Ala-NH2; Marfey's reagent; (S)-2-((5-Fluoro-2,4-dinitrophenyl)amino)propanamide
Appearance
Yellow solid
Purity
≥ 98 % (HPLC)
Density
1.592 g/cm3
Melting Point
>148 °C (dec.)
Boiling Point
544.5 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H9FN4O5/c1-4(9(11)15)12-6-2-5(10)7(13(16)17)3-8(6)14(18)19/h2-4,12H,1H3,(H2,11,15)/t4-/m0/s1
InChI Key
NEPLBHLFDJOJGP-BYPYZUCNSA-N
Canonical SMILES
CC(C(=O)N)NC1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])F

Nα-(2,4-Dinitro-5-fluorophenyl)-L-alanine amide, a specialized chemical compound with diverse applications in bioscience research and industrial settings, is the focus of the following. The key applications are presented with high perplexity and burstiness:

1. Fluorescent Labeling: Serving as a remarkably versatile fluorescent probe, Nα-(2,4-Dinitro-5-fluorophenyl)-L-alanine amide emerges as a crucial tool for tagging proteins and nucleic acids in scientific pursuits. Its distinctive fluorescence properties position it as the optimal choice for monitoring intricate biological processes under powerful microscopes, facilitating real-time tracking of molecular interactions and cellular activities with unparalleled precision.

2. Enzyme Assays: Within the realm of enzyme activity assessments, particularly those involving proteases and peptidases, this compound assumes a pivotal role. By integrating it as a substrate, researchers unlock the ability to evaluate enzyme kinetics and activity by quantifying the release of fluorescent or colorimetric signals. This approach not only deepens the understanding of enzyme functions but also empowers the precise screening of enzyme inhibitors, pushing the boundaries of enzymology research.

3. Drug Development: In the intricate landscape of pharmacological explorations, Nα-(2,4-Dinitro-5-fluorophenyl)-L-alanine amide emerges as a key player in testing the effectiveness and metabolism of pharmaceutical compounds. Its seamless integration into drug formulations and research methodologies facilitates the monitoring of drug distribution and interactions with biological targets, offering indispensable insights for refining drug design and delivery strategies with utmost efficacy.

4. Molecular Diagnostics: At the forefront of diagnostic assays, this compound plays a pivotal role in detecting specific biomolecules or pathogens with pinpoint accuracy. Through its selective binding to target molecules, it enables the visualization of diagnostic results using fluorescence, revolutionizing the development of sensitive and specific diagnostic tests for a wide spectrum of medical conditions. This advancement propels the field of molecular diagnostics into new realms of precision and efficiency.

1. Liquid chromatographic enantioseparation of spin-labelled beta-amino acids
Antal Péter, Roland Török, Karen Wright, Michel Wakselman, Jean Paul Mazaleyrat J Chromatogr A. 2003 Dec 22;1021(1-2):1-10. doi: 10.1016/j.chroma.2003.09.015.
Direct and indirect high-performance liquid chromatographic (HPLC) methods were developed for the enantioseparation of spin-labelled, cyclic, chiral beta-amino acids containing nitroxide free radicals, trans-3-amino- 1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (trans-POAC), cis-4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (cis-beta-TOAC) and their N-Fmoc-protected analogues, synthesized in racemic and enantiomerically pure forms. The direct method involved the use of a Chiralcel OD-RH column, while indirect separation was carried out by application of either 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate or (S)-N-(4-nitrophenoxycarbonyl)-phenylalanine methoxyethyl ester as chiral derivatizing agent. Use of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) as chiral derivatizing agent failed because of the low of yield of the derivatization reaction. Selection and variation of the mobile phase was restricted by the sensitivity of the spin-labelled amino acids to acidic conditions. Conditions affording the best resolution were found and the differences in separation capability of the methods were noted. The sequence of elution of the enantiomers was determined by different methods and, in the case of the beta-TOAC analogues, the absolute configurations of the enantiomers corresponding to each peak were identified.
2. Direct and indirect high-performance liquid chromatographic enantioseparation of beta-amino acids
Antal Péter, Anita Arki, Erika Vékes, Dirk Tourwé, László Lázár, Ferenc Fülöp, Daniel W Armstrong J Chromatogr A. 2004 Mar 26;1031(1-2):171-8. doi: 10.1016/j.chroma.2003.08.070.
Direct and indirect reversed-phase (RP) high-performance liquid chromatographic methods were developed for the separation of enantiomers of 18 unnatural beta-amino acids, including several beta-3-homo amino acids. The direct separations of the underivatized analytes were performed on chiral stationary phases (CSPs) containing macrocyclic glycopeptide antibiotic teicoplanin (Chirobiotic T column) and teicoplanin aglycone (Chirobiotic TAG column). The indirect method involved pre-column derivatization with a new chiral derivatizing agent (CDA), (S)-N-(4-nitrophenoxycarbonyl)phenylalanine methoxyethyl ester ((S)-NIFE), and subsequent separation of diastereomers on Discovery C18 and Hyperpep 300 C18 columns. The different methods were compared in systematic chromatographic examinations. The effects of organic modifier, mobile phase composition, pH and flow rate on the separation were investigated.
3. High-performance liquid chromatographic enantioseparation of beta-amino acids
A Péter, L Lázár, F Fülöp, D W Armstron J Chromatogr A. 2001 Aug 17;926(2):229-38. doi: 10.1016/s0021-9673(01)01078-0.
Direct and indirect high-performance liquid chromatographic methods were developed for the enantioseparation of beta-amino acids (beta-substituted-beta-alanines). Direct separation involved the application of chiral columns: Crownpak CR(+), Chirobiotic T and Chirobiotic R. Indirect separation was based on precolumn derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate or N-alpha-(2,4-dinitro-5-fluorophenyl)-L-alanineamide (Marfey's reagent), with subsequent separation on an achiral column. The chromatographic conditions were varied to achieve optimum separation.
Online Inquiry
Verification code
Inquiry Basket