Reaktionen von 1,5‐difluor‐2,4‐dinitrobenzol mit insulin 1. Mitt. Synthese von modellverbindungen

Abstract

ZUSAMMENFASSUNG:1,5-Difluor-2,4-dinitrobenzol wurde mit Glycin, DL-Phenylalanin, L -T~~O S~ und DL-LYsin derart umgesetzt, daB die monofunktionellen, bifunktionellen und gemischt bifunktioneilen Aminosaurederivate iiber die Ester gewonnen wurden. Die Verbindungen wurden durch Elementaranalyse, Papierchromatographie und Debyeogramm charakteiisiert. SUMMARY:By reaction of 1,5-difluoro-2,4-dinitrobenzene with glycine, DL-phenylalanine, L-tyrosine and DL-lysine, monofunctional, bifunctional and mixed bifunctional amino acid derivatives have been prepared through their esters. The compounds were characterized by elementary analysis, paper chromatography and the debyeogram.

Marfey's reagent: Past, present, and future uses of 1‐fluoro‐2,4‐dinitrophenyl‐5‐L‐alanine amide

“…This reagent, 1,5-difluoro-2,4-dinitrobenzene (DFDNB), was used by the two previously mentioned researchers for the cross-linking of proteins including insulin, silk, and wool. Zahn and Meienhofer [29] prepared monofunctional and bifunctional derivatives of DFDNB with amino acid esters and reported on separations using paper chromatography. They also reported on attempts to Figure 1.…”

“…This reagent, 1,5-difluoro-2,4-dinitrobenzene (DFDNB), was used by the two previously mentioned researchers for the cross-linking of proteins including insulin, silk, and wool. Zahn and Meienhofer [29] prepared monofunctional and bifunctional derivatives of DFDNB with amino acid esters and reported on separations using paper chromatography. They also reported on attempts to [23] considered the intramolecular hydrogen bonding of the L,L diasteromer to be stronger than that of the L, D diasteromer creating the physical property to effect a chromatographic separation.…”

My journey from wool research to insulin

“…Meienhofer began his diploma thesis in July 1953 [18]. In those days the covalent structure of the A and B chains [19,20] was known, but neither the position of the disulfide bonds nor the molecular weight had been established unambiguously.…”

Synthesis of a protein modifying agent. A water-soluble stable free radical

“…Gerig et al (7) prepared 1 from the commercially available stable free radical 4 and 4,6-dinitro-l,3-difluorobenzene. The relative ease of replacement of the first fluorine in 4,6-dinitro-1,3-difluorobenzene by amino groups, as well as the lessened reactivity of the second Auorine, was described by Zahn and Meienhoffer (9) and exploited by Cautrecasas and co-workers (8). The fluorine in B is still sufficiently reactive to be replaced by reactive amino groups in human serum albumin (7).…”