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Key Documents

D7906

Sigma-Aldrich

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

powder

Synonym(s):

FDAA, Marfey’s reagent

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About This Item

Empirical Formula (Hill Notation):
C9H9FN4O5
CAS Number:
Molecular Weight:
272.19
Beilstein/REAXYS Number:
6820069
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.25

form

powder

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

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Application

N-α-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide is suitable for use for the derivatization of amino acids. glutamate and analine present in cell wall. Derivatized D- and L-amino acids can be resolved and quantitated by HPLC.

Biochem/physiol Actions

N-α-(2,4-Dinitro-5-fluorophenyl)-L-alaninamide (FDAA) is a chiral derivatizing agent and is used routinely to improve the detection of underivatized amino acids in high performance liquid chromatography. Its usage is effective in separating stereoisomer.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The functional dlt operon of Clostridium butyricum controls the D-alanylation of cell wall components and influences cell septation and vancomycin-induced lysis
Wydau-Dematteis S, et al.
Anaerobe, 35, 105-114 (2015)
High concentrations of D-amino acids in human gastric juice
Nagata Y, et al.
Amino Acids, 32(1), 137-140 (2007)
A comparison of the direct and indirect LC methods for separating enantiomers of unusual glycine and alanine amino acid analogues
Peter A, et al.
Chromatographia, 56(1), S79-S89 (2002)
C3 and 2D C3 Marfey?s methods for amino acid analysis in natural products
Vijayasarathy S, et al.
Journal of Natural Products, 79(2), 421-427 (2016)
Purification of branched-chain amino acid aminotransferase from Helicobacter pylori NCTC 11637
Saito M, et al.
Amino Acids, 33(3), 445-449 (2007)

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