Journal ArticleDOI
Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models.
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TLDR
Results indicate that, based on chemical reactivity, peptide alkylation should occur in the order cysteine thiol > N-terminal amino > N epsilon-lysine = NIm-histidine, with side chain modifications occurring only with the more electrophilic QMs.About:
This article is published in Chemico-Biological Interactions.The article was published on 1997-11-28. It has received 73 citations till now. The article focuses on the topics: Protein alkylation & Amino acid.read more
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Drug delivery systems employing 1,4- or 1,6-elimination: poly(ethylene glycol) prodrugs of amine-containing compounds.
Richard B. Greenwald,Annapurna Pendri,Charles D. Conover,Hong Zhao,Yun H. Choe,Anthony Martinez,Kwok L. Shum,Shuiyun Guan +7 more
TL;DR: PEG conjugated specifiers or "triggers" are successfully designed as part of a double-prodrug strategy that relies, first, on enzymatic separation of PEG followed by the classical and rapid 1,4- or 1, 6-benzyl elimination reaction releasing the amine (drug) bound in the form of a carbamate.
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Covalent inhibitors of glycosidases and their applications in biochemistry and biology
TL;DR: Some of the compounds used to covalently modify glycosidases, their use in residue identification, structural and mechanistic investigations, and finally their applications, both in vitro and in vivo, to complex biological systems are discussed.
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Measurement and estimation of electrophilic reactivity for predictive toxicology.
Johannes A.H. Schwöbel,Yana K. Koleva,Steven J. Enoch,Fania Bajot,Mark Hewitt,Judith C. Madden,David W. Roberts,Terry W Schultz,Mark T. D. Cronin +8 more
TL;DR: Measurement and Estimation of Electrophilic Reactivity for Predictive Toxicology Johannes A. H. Schw€obel, Yana K. Koleva, Steven J. Enoch, Fania Bajot, Mark Hewitt, Judith C.Madden, and Mark T. Schultz.
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Development of a catheter functionalized by a polydopamine peptide coating with antimicrobial and antibiofilm properties
TL;DR: A simple yet effective immobilization strategy to tether a potent synthetic antimicrobial peptide, CWR11, onto catheter-relevant surfaces is reported, demonstrating the proof-of-concept potential of a polydopamine-CWR11-functionalized catheter to combat CAUTIs.
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Alkylation of amino acids and glutathione in water by o-quinone methide. Reactivity and selectivity.
TL;DR: These are the first direct reaction rate measurements of nucleophilic addition to the parent o-quinone methide, and a thermal and photochemical reversibility of the alkylation process opens a new perspective for the use and application of such adducts as o-QM molecular carriers.
References
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Data for biochemical research (third edition) by R M C Dawson, D C Elliott, W H Elliott and K M Jones, pp 580. Oxford Science Publications, OUP, Oxford, 1986. £35/$59. ISBN 0‐19‐855358‐7
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Chemical Modifications of Biopolymers by Quinones and Quinone Methides
TL;DR: Several major and important new results have emerged from the development and applications of modern methods of sample separation and from solid-state NMR spectroscopy, namely, the chemical modification of biopolymers.
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Biological and toxicological consequences of quinone methide formation.
TL;DR: The role of quinone methides in the synthesis of several complex plant and animal polymers, including lignin, cuticle and melanin, and the role of alkylphenols in these various processes is reviewed.
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Effects of Modifying Structure on Electrophilic Reactions with Biological Nucleophiles
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Cresol Isomers: Comparison of Toxic Potency in Rat Liver Slices
TL;DR: It is demonstrated that p-cresol is the most toxic cResol isomer in rat liver tissue and that its toxicity is dependent on the formation of a reactive intermediate, and the mechanism(s) of toxicity of the o- and m-isomers may differ from that of p- cresol.