All Photos(4)

D7906

Sigma-Aldrich

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

powder

Synonym(s):
Marfey’s reagent, FDAA
Empirical Formula (Hill Notation):
C9H9FN4O5
CAS Number:
Molecular Weight:
272.19
Beilstein:
6820069
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.25

form

powder

Quality Level

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.

Packaging

25 mg in poly bottle
100 mg in glass bottle

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

High concentrations of D-amino acids in human gastric juice
Nagata Y, et al.
Amino Acids, 32(1), 137-140 (2007)
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)
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)
Purification of branched-chain amino acid aminotransferase from Helicobacter pylori NCTC 11637
Saito M, et al.
Amino Acids, 33(3), 445-449 (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)

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