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Merck
CN

71478

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

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

Key Documents

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Product Name

Nα-(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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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

Nα-(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

Exclamation mark
GHS07

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0069
BCCM9307
BCCL4997
BCCK1844
BCCH0669

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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)
Sonja Hess et al.
Analytical biochemistry, 311(1), 19-26 (2002-11-21)
Silk fibroins from moth larvae and spiders are composed of highly repetitive Ala- and Gly-rich blocks that determine their structure, properties, and function. To investigate the metabolic integration of isotopically labeled amino acids in the excreted silk, the enrichment of
Michael J Berna et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 846(1-2), 359-363 (2006-09-12)
The ability to selectively measure serine enantiomer concentrations in rat brain microdialysate is essential during drug discovery to study the interaction of d-serine with the N-methyl-d-aspartate (NMDA) subtype of the glutamate receptor. NMDA receptor-stimulating agents, such as d-serine, have been
G Szókán et al.
Journal of chromatography, 444, 115-122 (1988-07-01)
Reversed-phase high-performance liquid chromatography and pre-column derivatization with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) were used for monitoring racemization in peptides, amino acids and their derivatives by separation of optical isomers of amino acids. The technique was applied to the analysis of
R Bhushan et al.
Amino acids, 36(3), 571-579 (2008-07-10)
Some non-protein alpha-amino acids were derivatized with 1-fluoro-2,4-dinitrophenyl-5-L-alaninamide (Marfey's reagent, MR, FDNP-L-Ala-NH(2),) and four of its structural variants FDNP-L-Phe-NH(2), FDNP-L-Val-NH(2), FDNP-L-Leu-NH(2) and FDNP-L-Pro-NH(2). The resultant diastereomers were separated by normal and reversed phase thin layer chromatography (TLC) and reversed phase
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