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Marfey’s Reagent (FDAA)


Separate and measure amino acid optical isomers by reverse-phase chromatography.

Pierce FDAA (Marfey's Reagents)

Thermo Scientific Pierce Marfey's Reagent (FDAA) reacts with primary amines to enable the separation and quantitation of optical isomers of amino acids by reverse-phase chromatography quick and easy.

FDAA is 1-fluoro-2-4-dinitrophenyl-5-L-alanine amide, also called Marfey's reagent. The compound reacts with primary amines and is used as a derivatization reagent for UV detection in liquid chromatography methods. The reagent provides for detection at 340nm with nanomole sensitivity. FDAA derivatives of D-amino acids exhibit strong intramolecular bonding, which reduces their polarity relative to the corresponding L-amino acid derivatives. Consequently, the D-derivatives are selectively retained on reverse phase columns and elute much later than corresponding L-derivatives.

Highlights:

  • For precolumn derivatization of primary amines for detection by UV absorbance (λmax = 340nm)
  • Provides nanomole sensitivity in typical HPLC applications with amino acids
  • Reaction products enable chiral separation of D- and L-amino acids
  • Following reverse-phase HPLC, derivatives have an extinction coefficient of 3 x 10^4M-1cm-1

Reagent Properties:

  • Alternative names: FDAA, Marfey's Reagent
  • Chemical name: 1-fluoro-2-4-dinitrophenyl-5-L-alanine amide; N2-(5-Fluoro-2,4-dinitrophenyl)-L-alaninamide
  • Reactive toward: Primary amines (–NH2)
  • Chemical formula: C9H9FN4O5
  • CAS number: 95713-52-3
  • Molecular weight: 272.19
  • Form: Bright yellow or orange crystals or powder, free of particulate matter

Product Details:

FDAA derivatives can be separated with simple linear gradient of triethylamine phosphate/acetonitrile on a Spheri-5 RP-18 HPLC cartridge column. FDAA reduces the need for a chiral column because the D-derivatives are retained on the column, eluting after the L-derivatives. The derivatization is easy to perform and completed in 90 minutes, resulting in derivatives that are stable for at least 48 hours.

Chemical structure of FDAA (Marfey's Reagent) Chemical structure of Marfey's Reagent (FDAA).

General References:

  1. Marfey, P., et al. (1984). Carlsberg Res. Comm. 49, 585-590.
  2. Marfey, P., et al. (1984). Carlsberg Res. Comm. 49, 591-596.
  3. Szókán, et al. (1988). Applications of Marfey's Reagent in racemization studies of amino acids and peptides. J. Chrom. 444, 115-122.
  4. Aberhart, D.J., et al. (1985). Separation by high-performance liquid chromato-graphy of (3R)- and 3(S)-beta-Leucine as diastereomeric derivatives. 151, 88-91.
  5. Martinez del Pozo, et al. (1989). Stereospecificity of reactions catalyzed by bacterial D-amino transaminase. J. Biol. Chem. 264(30), 17784-17789.
  6. Bhushan, R. and Bruckner, H. (2004). Marfey's reagent for chiral amino acid analysis: A review. Amino Acids 27:231-47.

Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
48895 FDAA (Marfey's Reagent)
Formulation: 1-Fluoro-2,4-dinitrophenyl-5-L-alanine amide
Sufficient For: Preparing 5mL of 1% solution in acetone for use at 200μL per typical experiment (approx. 25 uses)
50mg Product Instructions for product #48895 FDAA (Marfey's Reagent) MSDS for product #48895 FDAA (Marfey's Reagent) Certificate of Analysis for product #48895 FDAA (Marfey's Reagent) $87.00

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Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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