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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
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grade

derivatization grade (chiral)

Quality Level

100

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

SMILES string

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

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

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.

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).

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

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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
BCCH0669
BCCG4642
BCCF8181
BCCF3030
BCCD8951

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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)
J G Adamson et al.
Analytical biochemistry, 202(1), 210-214 (1992-04-01)
A chromatographic assay has been developed to quantitate racemization occurring during attachment of protected amino acids to peptide synthesis resins. Acidolytic cleavage of deprotected amino acids from supports and subsequent derivatization with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (Marfey's reagent) gave diastereomers separable by
R Bhushan et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 879(29), 3148-3161 (2011-07-09)
The present paper describes an updated knowledge and status on Marfey's reagent (MR), 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (FDNP-L-Ala-NH(2)). The reagent is used for pre-column derivatization of amino acids followed by HPLC separation of the diastereomers so formed. Emphasis is put on the
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Global Trade Item Number

SKUGTIN
71478-50MG04061832848716