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1-Fluoro-2,4-dinitrobenzene (commonly called Sanger's reagent, dinitrofluorobenzene, DNFB or FDNB) is a chemical that reacts with the N-terminal amino acid of polypeptides. This can be helpful for sequencing proteins.




Preparation


In 1936, Gottlieb presented a synthesis in which 1-chloro-2,4-dinitrobenzene reacted with potassium fluoride (KF) in nitrobenzene:




Uses



In 1945, Frederick Sanger described its use for determining the N-terminal amino acid in polypeptide chains, in particular insulin. Sanger's initial results suggested that insulin was a smaller molecule than previously estimated (molecular weight 12,000), and that it consisted of four chains (two ending in glycine and two ending in phenylalanine), with the chains cross-linked by disulfide bonds. Sanger continued work on insulin, using dinitrofluorobenzene in combination with other techniques, eventually resulted in the complete sequence of insulin (consisting of only two chains, with a molecular weight of 6,000).
Following Sanger's initial report of the reagent, the dinitrofluorobenzene method was widely adopted for studying proteins, until it was superseded by other reagents for terminal analysis (e.g., dansyl chloride and later aminopeptidases and carboxypeptidases) and other general methods for sequence determination (e.g., Edman degradation).
Dinitrofluorobenzene reacts with the amine group in amino acids to produce dinitrophenyl-amino acids. These DNP-amino acids are moderately stable under acid hydrolysis conditions that break peptide bonds. The DNP-amino acids can then be recovered, and the identity of those amino acids can be discovered through chromatography. More recently, Sanger's reagent has also been used for the rather difficult analysis of distinguishing between the reduced and oxidized forms of glutathione and cysteine in biological systems in conjunction with HPLC. This method is robust enough that it can be performed in such complex matrices as blood or cell lysate.




See also


N-Terminal amino acid analysis




References






Literature


Schaefer, T. (1962). "The Proton Magnetic Resonance Spectrum of 1-Fluoro-2,4-Dinitrobenzene". Canadian Journal of Chemistry. 40 (3): 431–433. doi:10.1139/v62-068.
Nageswara Rao, B.D. (1964). "The1H and19F resonance spectra of 1-fluoro-2,4-dinitrobenzene". Molecular Physics. 7 (4): 307–310. Bibcode:1964MolPh...7..307N. doi:10.1080/00268976300101071.
Wilkins, A.; Small, R. W. H. (1991). "Structure of 1-fluoro-2,4-dinitrobenzene". Acta Crystallographica Section C. 47 (1): 220–221. Bibcode:1991AcCrC..47..220W. doi:10.1107/S0108270190007326.




External links


Fluorodinitrobenzene – 1-fluoro-2,4-dinitro-benzene (wikigenes.org)

Kata Kunci Pencarian:

• 1-Fluoro-2,4-dinitrobenzene
• Halex process
• California Proposition 65 list of chemicals
• Frederick Sanger

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Daftar Isi

• 1-Fluoro-2,4-dinitrobenzene - Wikipedia
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• Dinitrofluorobenzene | C6H3FN2O4 | CID 6264 - PubChem
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1-Fluoro-2,4-dinitrobenzene - Wikipedia

1-Fluoro-2,4-dinitrobenzene (commonly called Sanger's reagent, dinitrofluorobenzene, DNFB or FDNB) is a chemical that reacts with the N-terminal amino acid of polypeptides. This can be helpful for sequencing proteins.

1-Fluoro-2,4-dinitrobenzene = 99 70-34-8 - MilliporeSigma

1-Fluoro-2,4-dinitrobenzene is a contact-sensitizing hapten, commonly used in experimental studies on contact hypersensitivity, inducing itch model, and atopic dermatitis. Mast cell activation is a key step in the DNFB induced sensitivity.

Dinitrofluorobenzene | C6H3FN2O4 | CID 6264 - PubChem

1-fluoro-2,4-dinitrobenzene is the organofluorine compound that is benzene with a fluoro substituent at the 1-position and two nitro substituents in the 2- and 4-positions. It has a role as an agrochemical, a protein-sequencing agent, an EC 2.7.3.2 (creatine kinase) inhibitor, an allergen, a chromatographic reagent and a spectrophotometric reagent.

1-Fluoro-2,4-dinitrobenzene 99% | Sigma-Aldrich - MilliporeSigma

1-Fluoro-2,4-dinitrobenzene 99%; CAS Number: 70-34-8; EC Number: 200-734-3; Synonyms: 2,4-Dinitro-1-fluorobenzene,DNFB,DNPF,FDNB,Sanger reagent; Linear Formula: (O2N)2C6H3F at Sigma-Aldrich

1-Fluoro-2,4-dinitrobenzene, 99%, Thermo Scientific Chemicals - Fisher Sci

1-Fluoro-2,4-dinitrobenzene is used to identify the amino acid sequence. It reacts with amino group of amino acids to yield dinitrophenyl-amino acids. It is also used in chromatographic methods. Further, it acts as an alkylating agent used in …

1-fluoro-2,4-dinitrobenzene - an overview | ScienceDirect Topics

Sanger reagent named 1-fluoro-2,4-dinitrobenzene (DNFB) is selectively used for the N-side (terminal) determination of peptide sequence. Usually, dinitrophenyl (DNP) derivatives were formed when any basic amino acid was treated with DNFB.

SAFETY DATA SHEET - Fisher Sci

1. Identification Product Name 1-Fluoro-2,4-dinitrobenzene Cat No. : A11871 CAS No 70-34-8 Synonyms 1-Fluoro-2,4-dinitrobenzene; DNF; Sanger`s Reagent Recommended Use Laboratory chemicals. Uses advised against Food, drug, pesticide or biocidal product use. Details of the supplier of the safety data sheet 2. Hazard(s) identification Classification

1-Fluoro-2,4-dinitrobenzene - MilliporeSigma

1-Fluoro-2,4-dinitrobenzene is a color labeling agent, mainly used for detecting primary and secondary amines.

1-Fluoro-2,4-dinitrobenzene, 99%, Thermo Scientific Chemicals

1-Fluoro-2,4-dinitrobenzene is used to identify the amino acid sequence. It reacts with amino group of amino acids to yield dinitrophenyl-amino acids. It is also used in chromatographic methods. Further, it acts as an alkylating agent used in …

Benzene, 1-fluoro-2,4-dinitro- - NIST Chemistry WebBook

The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment.