N_α-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide

Name: N<SUB>α</SUB>-(2,4-Dinitro-5-fluorophenyl)-<SC>L</SC>-alaninamide
Brand: SIAL

derivatization grade (chiral), LiChropur^™, ≥99.0%

Synonym(s):

FDAA, Marfey’s reagent

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About This Item

Empirical Formula (Hill Notation):

C₉H₉FN₄O₅

CAS Number:

95713-52-3

Molecular Weight:

272.19

UNSPSC Code:

23151816

NACRES:

NA.22

PubChem Substance ID:

329763313

MDL number:

MFCD00042049

Beilstein/REAXYS Number:

6820069

Product Name

N_α-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide, derivatization grade (chiral), LiChropur^™, ≥99.0%

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

SMILES string

C[C@H](Nc1cc(F)c(cc1[N+]([O-])=O)[N+]([O-])=O)C(N)=O

InChI key

NEPLBHLFDJOJGP-BYPYZUCNSA-N

grade

derivatization grade (chiral)

assay

≥99.0% (sum of enantiomers, TLC)
≥99.0%

form

powder

optical activity

[α]20/D +56±2°, c = 1% in acetone

optical purity

enantiomeric ratio: ≥99.5:0.5 (HPLC)

quality

LiChropur^™

technique(s)

HPLC: suitable

storage temp.

2-8°C

Quality Level

100

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Related Categories

Analytical Chemistry

Analytical Reagents

Chromatography & Spectroscopy Reagents

Application

FDAA was used as derivatizing reagent, in a study performed to understand unusual amino acids using reversed phase high performance liquid chromatography-electrospray ionization mass spectrometry (RPHPLC-ESI-MS).

General description

N_α-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide (FDAA) is a chiral derivatizing agent (CDA), has high enantioselectivity but low sensitivity as compared to other CDAs. It is generally used to assign the stereochemistry of amino acids in trace amounts.

Other Notes

Derivatization reagent for the assay of unusual chiral α-amino acid analogs

Discover LiChropur reagents ideal for HPLC or LC-MS analysis

Legal Information

LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography-electrospray ionization mass spectrometry.

Hess S

Journal of Chromatography A, 1035(2), 211-219 (2004)

Peptide chiral purity determination: hydrolysis in deuterated acid, derivatization with Marfey's reagent and analysis using high-performance liquid chromatography-electrospray ionization-mass spectrometry.

D R Goodlett et al.

Journal of chromatography. A, 707(2), 233-244 (1995-07-21)

A high-performance liquid chromatography-electrospray ionization-mass spectrometric (LC-ESI-MS) method is presented that allows rapid and accurate determination of amino acid chiral purity in a peptide. Peptides are hydrolyzed in hydrochloric acid-d1/acetic acid-d4 and then converted to diastereomers by derivatization with 1-fluoro-2,4-dinitrophenyl-5-L-alanine

Stereochemical heterogeneity in Verongid sponge metabolites. Absolute stereochemistry of (+)-fistularin-3 and (+)-11-epi-fistularin-3 by microscale LCMS-Marfey's analysis.

Evan W Rogers et al.

Journal of natural products, 68(6), 891-896 (2005-06-25)

The absolute configurations of fistularin-3, 11-epi-fistularin-3, and a related bis-oxazolidinone were determined by microscale hydrolysis followed by derivatization with 1-fluoro-2,4-dinitrophenyl-5-l-alaninamide. Samples of fistularin-3 from Verongid marine sponges collected in the Great Barrier Reef (Australia), Baía de Todos os Santos (Brazil)

Separation and quantification of D- and L-phosphoserine in rat brain using N alpha-(2,4-dinitro-5-fluorophenyl)-L-alaninamide (Marfey's reagent) by high-performance liquid chromatography with ultraviolet detection.

D B Goodnough et al.

Journal of chromatography. B, Biomedical applications, 672(2), 290-294 (1995-10-20)

D-Serine has recently been described to be present in the brain at high concentrations. However, while prior research has demonstrated that L-phosphoserine is the major precursor of L-serine in the brain, the possible role of D-phosphoserine as the direct precursor

Esterification of 9-fluorenylmethoxycarbonyl-glycosylated serine and cysteine derivatives with an hydroxymethyl resin.

E Harth-Fritschy et al.

The journal of peptide research : official journal of the American Peptide Society, 50(6), 415-420 (1998-01-24)

Esterification of glycosylated serine and cysteine derivatives with a 4-alkoxybenzyl alcohol (Wang) resin is described. The classical methods of ester bond formation (symmetrical anhydride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate [TBTU]/4-dimethylaminopyridine [DMAP] with or without 1-hydroxybenzotriazole [HOBT], pentafluorophenyl [Pfp] esters gave high percentages of

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Nα-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide

derivatization grade (chiral), LiChropur™, ≥99.0%