Receptor site labeling through functional groups. 2. Reactivity of maleimide groups

Miyadera, Tetsuo; Kosower, Edward M.

doi:10.1021/jm00275a024

Cited by 30 publications

(16 citation statements)

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“…Therefore, maleimide reacts fast and selectively with thiol groups. 77 Such selectivity may induce toxic effects by converting cysteine residues of proteins, in analogy to α,β-unsaturated enedials and oxoenals produced by oxidation of phenols. 78 Formamide is polar and biodegradable and is less prone to be bioaccumulated in aquatic organisms.…”

Section: Discussionmentioning

confidence: 99%

Reactions of pyrrole, imidazole, and pyrazole with ozone: kinetics and mechanisms

Tekle-Röttering

Lim

Reisz

et al. 2020

Environ. Sci.: Water Res. Technol.

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Section: Discussionmentioning

confidence: 99%

Reactions of pyrrole, imidazole, and pyrazole with ozone: kinetics and mechanisms

Tekle-Röttering

Lim

Reisz

et al. 2020

Environ. Sci.: Water Res. Technol.

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“…Maleimide and NHS-ester derived probes are commonly used to modify proteins, as they are reactive with thiol and amino-groups of cysteine and lysine, respectively 13–15 . While cysteines and lysines can be introduced at the N-terminus of a protein, the use of side chain-reactive probes lacks selectivity and may also compromise the active site of the protein being labeled.…”

Section: Introductionmentioning

confidence: 99%

Site-specific N-terminal labeling of proteins using sortase-mediated reactions

et al. 2013

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For many proteins, the N- or the C-terminus make essential contributions to substrate binding, for protein-protein interactions, or for anchoring the proteins to a membrane. In other circumstances, at least one of the termini is buried within the protein, rendering it inaccessible to labeling. The possibility of selective modification of one of the protein’s termini may present unique opportunities for biochemical and biological applications. We describe sortase-mediated reactions to selectively label the N-terminus of a protein with a variety of functional groups. If sortase, the protein of interest, and a suitably functionalized label are available, the reactions usually require less than 3 hours.

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“…In the studied compounds, due to the weak basicity of the N=N group [68], it can act as proton acceptor which can accept proton at very low pH values ~2.0 [69]. Thus, its pK values cannot be determined in our work.…”

Section: P-n(c2h5)2 > P-oh > O-ch3 > -H > Naphthy > P-hso3 > O-cooh >mentioning

confidence: 98%

Spectrophotometric studies on some arylazo diamino pyrimidinol in organic solvents and in buffer solutions

et al. 2014

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KEYWORDSThe spectral behavior of some new arylazo-2,6-diamino-4-pyrimidinol in pure and mixed organic solvents and buffer solutions of varying pH have been studied. The observed bands are assigned to the possible electronic transition. The band appearing in the visible region is assigned to →* transition involving -electronic system of the whole compounds, associated with intramolecular charge transfer. This charge transfer seems to originate from the aryl moiety to the pyrimidine ring which is characterized by accepting character. This behavior can be explained that these compounds exist in the hydroxyazo-quinoid hydrazon tautomreic explained equilibrium. The possibility of the formation of -H-bond solvated molecular complex between the molecule of azo 2,6-diaminopyrimidinol and proton-acceptor solvents of DMSO and DMF molecular were discussed. The pK values of these compounds were determined and on the basis of the relative contribution of acidic basic character of respective species. pK values Mixed solvents Buffer solutions Spectra behavior Molecular complex Arylazo diaminopyrimidinol

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Receptor site labeling through functional groups. 2. Reactivity of maleimide groups

Cited by 30 publications

References 0 publications

Reactions of pyrrole, imidazole, and pyrazole with ozone: kinetics and mechanisms

Reactions of pyrrole, imidazole, and pyrazole with ozone: kinetics and mechanisms

Site-specific N-terminal labeling of proteins using sortase-mediated reactions

Spectrophotometric studies on some arylazo diamino pyrimidinol in organic solvents and in buffer solutions

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