Ueber die Oxydation des Paraphenylendiamins

Bandrowski, Ernst v.

doi:10.1002/cber.18940270194

Cited by 46 publications

(13 citation statements)

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“…In 1894, Bandrowski already described a trimeric PPD derivative obtained by the oxidation of PPD with oxygen or ferricyanide in ammoniacal solution [24]. Later on, this compound was named after him ( Table 2).…”

Section: Trimeric Reaction Products Bandrowski's Basementioning

confidence: 97%

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Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Meyer

Fischer

2015

Environ Sci Eur

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Section: Trimeric Reaction Products Bandrowski's Basementioning

confidence: 97%

“…The elucidation of their reaction pathways and products has a long history, starting with the pioneering work of Bandrowski [24]. The topic remains the object of ongoing research [25,26].…”

Section: Introductionmentioning

confidence: 99%

Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Meyer

Fischer

2015

Environ Sci Eur

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“…8 We observed that in the presence of sodium periodate, N-acyl phenylenediamines (such as 1, Figure 1a) underwent a clean trimerization reaction to afford red dye derivatives (3) described by Bandrowski in the late 1890s. 9 This reaction proceeded in minutes in aqueous solution buffered at pH 6.5 and was unaffected by the presence of complex biomolecules and polar functional groups. From this starting point, we first sought to stop the trimerization reaction through the addition of alkyl groups to the aniline nitrogen, Figure 1b.…”

Section: Bioconjugation Strategymentioning

confidence: 99%

Development of Oxidative Coupling Strategies for Site-Selective Protein Modification

ElSohly

Francis

2015

Acc. Chem. Res.

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As the need to prepare ever more complex but well-defined materials has increased, a similar need for reliable synthetic strategies to access them has arisen. Accordingly, recent years have seen a steep increase in the development of reactions that can proceed under mild conditions, in aqueous environments, and with low concentrations of reactants. To enable the preparation of well-defined biomolecular materials with novel functional properties, our laboratory has a continuing interest in developing new bioconjugation reactions. A particular area of focus has been the development of oxidative reactions to perform rapid site- and chemoselective couplings of electron rich aromatic species with both unnatural and canonical amino acid residues. This Account details the evolution of oxidative coupling reactions in our laboratory, from initial concepts to highly efficient reactions, focusing on the practical aspects of performing and developing reactions of this type. We begin by discussing our rationale for choosing an oxidative coupling approach to bioconjugation, highlighting many of the benefits that such strategies provide. In addition, we discuss the general workflow we have adopted to discover protein modification reactions directly in aqueous media with biologically relevant substrates. We then review our early explorations of periodate-mediated oxidative couplings between primary anilines and p-phenylenediamine substrates, highlighting the most important lessons that were garnered from these studies. Key mechanistic insights allowed us to develop second-generation reactions between anilines and anisidine derivatives. In addition, we summarize the methods we have used for the introduction of aniline groups onto protein substrates for modification. The development of an efficient and chemoselective coupling of anisidine derivatives with tyrosine residues in the presence of ceric ammonium nitrate is next described. Here, our logic and workflow are used to highlight the challenges and opportunities associated with the optimization of site-selective chemistries that target native amino acids. We close by discussing the most recent reports from our laboratory that have capitalized on the unique reactivity of o-iminoquinone derivatives. We discuss the various oxidants and conditions that can be used to generate these reactive intermediates from appropriate precursors, as well as the product distributions that result. We also describe our work to determine the nature of iminoquinone reactivity with proteins and peptides bearing free N-terminal amino groups. Through this discussion, we hope to facilitate the use of oxidative approaches to protein bioconjugation, as well as inspire the discovery of new reactions for the site-selective modification of biomolecular targets.

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“…26 We had previously found that anilines reacted rapidly and cleanly with N -acyl phenylene diamines in the presence of sodium periodate. 27 The resulting “Bandrowski bases” 28 were stable with respect to hydrolysis across a wide pH range and could withstand strong reductants, oxidants, nucleophiles, and high temperatures. Although the original reaction yielded a trimeric species, we found that the product symmetry could be broken by adding two alkyl groups to the phenylene diamine group.…”

Section: Targeted Imaging and Drug Delivery Agents Based On Bacteriopmentioning

confidence: 99%

Using Synthetically Modified Proteins to Make New Materials

2011

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CONSPECTUS The uniquely diverse structures and functions of proteins offer many exciting opportunities for creating new materials with advanced properties. Exploiting these capabilities requires a set of versatile chemical reactions that can attach nonnatural groups to specific locations on protein surfaces. Over the years, we and others have developed a series of new techniques for protein bioconjugation, with a particular emphasis on achieving high site selectivity and yield. Using these reactions, we have been able to prepare a number of new materials with functions that depend on both the natural and the synthetic components. In this Account, we discuss our progress in protein bioconjugation over the past decade, focusing on three distinct projects. We first consider our work to harness sunlight artificially by mimicking features of the photosynthetic apparatus, with its beautifully integrated system of chromophores, electron transfer groups, and catalytic centers. Central to these photosystems are light-harvesting antennae having hundreds of precisely aligned chromophores with positions that are dictated by the proteins within the arrays. Our approach to generating similar arrangements involves the self-assembly of tobacco mosaic virus coat proteins bearing synthetic chromophore groups. These systems offer efficient light collection, are easy to prepare, and can be used to build complex photocatalytic systems through the modification of multiple sites on the protein surfaces. We then discuss protein-based carriers that can deliver drugs and imaging agents to diseased tissues. The nanoscale agents we have built for this purpose are based on the hollow protein shell of bacteriophage MS2. These 27 nm capsids have 32 pores, which allow the entry of relatively large organic molecules into the protein shell without requiring disassembly. Our group has developed a series of chemical strategies that can install dyes, radiolabels, MRI contrast agents, and anti-cancer drugs on the inside surface of these capsids. We have also developed methods to decorate the external surfaces with binders for specific proteins on cancer cells. As a third research area, our group has developed protein–polymer hybrid materials for water remediation. To reduce the toxicity of heavy metals in living cells, Nature has evolved metallothioneins, which are sulfur-rich polypeptides that bind mercury, cadmium, and other toxic ions at sub-parts-per-billion concentrations. Unfortunately, these proteins are very difficult to incorporate into polymers, largely because typical protein modification reactions target the very cysteine, lysine, and carboxylate-containing residues that are required for their proper function. To address this challenge, we developed a new way to attach these (and many other) proteins to polymer chains by expressing them as part of an N- and C-terminal modification “cassette.” The resulting materials retain their selectivity and can remove trace amounts of toxic metal ions from ocean water. Each of these examples has pres...

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Ueber die Oxydation des Paraphenylendiamins

Cited by 46 publications

References 1 publication

Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Development of Oxidative Coupling Strategies for Site-Selective Protein Modification

Using Synthetically Modified Proteins to Make New Materials

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