1-Fluoro-2,4-dinitrobenzene

changed 477207705 1-Fluoro-2,4-dinitrobenzene.svg 130px 1-Fluoro-2,4-dinitrobenzene-3D-spacefill.png 160 DNFB molecule 1-Fluoro-2,4-dinitrobenzene DinitrofluorobenzeneSanger's reagent DNFB, FDNB correct chemspider correct EBI 53049 21106037 1/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H LOTKRQAVGJMPNV-UHFFFAOYAZ correct EBI 167423 correct chemspider 1S/C6H3FN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H correct chemspider LOTKRQAVGJMPNV-UHFFFAOYSA-N correct CAS 70-34-8 6264 correct FDA D241E059U6 O=[N+]([O-])c1cc(ccc1F)[N+]([O-])=O 6 3 1 2 4 yellow crystals 1.4718 g·cm−3 (54 °C) 25.8 CRC Handbook of Chemistry and Physics, 90. edition, CRC Press, Boca Raton, Florida, 2009, 978-1-4200-9084-0, Section 3, Physical Constants of Organic Compounds, p. 3-260. 296 301 311 331 340 350 260 280 282 315 06 50 mg/kg-1 100 mg/kg-1 Oxford MSDS 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: Billroth Gottlieb Hans 1936 The Replacement of Chlorine by Fluorine in Organic Compounds J. Am. Chem. Soc. 58 3 532–533 10.1021/ja01294a502 450px|Synthesis of 1-fluoro-2,4-dinitrobenzene from 1-chloro-2,4-dinitrobenzene in nitrobenzene with potassium fluoride Uses thumb|left|150px|Frederick Sanger In 1945, Frederick Sanger described its use for determining the N-terminal amino acid in polypeptide chains, in particular insulin. Sanger F The free amino groups of insulin The Biochemical Journal 39 5 507–15 1945 16747948 1258275 10.1042/bj0390507 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).Joseph Fruton, Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology. New Haven: Yale University Press, 1999. p. 216. 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.10.1016/S0378-4347(01)00298-5 11585123 A new and versatile method for determination of thiolamines of biological importance Journal of Chromatography B: Biomedical Sciences and Applications 761 1 1–12 2001 Dominick Pamela K. Cassidy Pamela B. Roberts Jeanette C. 10.1016/j.jchromb.2011.05.026 21665555 RP-HPLC method for quantitative determination of cystathionine, cysteine and glutathione: An application for the study of the metabolism of cysteine in human brain Journal of Chromatography B 879 21 2005–2009 2011 Bronowicka-Adamska Patrycja Zagajewski Jacek Czubak Jerzy Wróbel Maria thumb|360px|left|Sanger's method of peptide end-group analysis: A derivatization of N-terminal end with Sanger's reagent (DNFB), B total acid hydrolysis of the dinitrophenyl peptide See also N-Terminal amino acid analysis References Literature 10.1139/v62-068 The Proton Magnetic Resonance Spectrum of 1-Fluoro-2,4-Dinitrobenzene Canadian Journal of Chemistry 40 3 431–433 1962 Schaefer T. free 10.1080/00268976300101071 The1H and19F resonance spectra of 1-fluoro-2,4-dinitrobenzene Molecular Physics 7 4 307–310 1964 Nageswara Rao B.D. 1964MolPh...7..307N 10.1107/S0108270190007326 Structure of 1-fluoro-2,4-dinitrobenzene Acta Crystallographica Section C 47 220–221 1991 Wilkins A. Small R. W. H. 1 1991AcCrC..47..220W External links Fluorodinitrobenzene – 1-fluoro-2,4-dinitro-benzene (wikigenes.org) Category:Nitrobenzene derivatives Category:Fluoroarenes