Kristina Görmer, Herbert Waldmann, Luc Brunsveld. By continuing you agree to the use of cookies. Find more information about Crossref citation counts. It has the same HPLC retention time as the product formed from cysteine when sequencing proteins alkylated with acrylamide. In lieu of an abstract, this is the article's first page. Please note: If you switch to a different device, you may be asked to login again with only your ACS ID. Prior to sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) analysis, the protein solutions (except for the one containing p21) were mixed with an equal volume of a buffer containing 0.9 M Tris-HCl, pH 8.45, 24% glycerol, 8% SDS, 0.01% coomassie G, 0.01% phenol red, and 5 mM DTT. Finally, PTH-Cys-S-Pam was synthesized chemically. The Center is funded by U.S. Department of Energy Grant DE-FG-88-ER13969 as a part of the USDA/DOE/NSF Plant Science Centers Program. Cysteine alkylation was also used as a tool for the identification of cysteine-containing peptides. PTH-Cys-S-Pam was first noticed during sequencing polypeptides blotted onto polyvinylidene difluoride membranes from polyacrylamide gels, in which cysteine had reacted with residual unpolymerized acrylamide. Using this procedure 37 the alkylation of l-cysteine with a series of alkyl halides was carried out.The results are given in Table 1.The yields of isolated products were very high, even for trans,trans-farnesyl, trans-geranyl or dodecyl bromides, and in some cases yields were almost quantitative.A lower yield was observed for highly soluble S-tert-butyloxy carbonylmethyl-l-cysteine … Christopher L. Brown, Margaret M. Harding. You have to login with your ACS ID befor you can login with your Mendeley account. Cysteine in proteins is easily alkylated by reaction of proteins in aqueous solution with acrylamide. In comparison with its acid derivative, iodoacetate, iodoacetamide reacts substantially faster. The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. All such fractions were pooled and the total sample volume was reduced by The protein sequencer was obtained with funds from NSF Grant BBS88-04992 (NSF Biological Centers Program). Find more information about Crossref citation counts. This article is cited by Iodoacetamide is an irreversible inhibitor of all cysteine peptidases, with the mechanism of inhibition occurring from alkylation of the catalytic cysteine residue (see schematic). The synthetic compound is unstable in neutral solution, but can be stabilized by acidification. Please reconnect. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. Cysteine alkylation was also used as a tool for the identification of cysteine-containing peptides.

Copyright © 2020 Elsevier B.V. or its licensors or contributors. Studies on oriented and reversible immobilization of glycoprotein using novel boronate affinity gel.

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. Using a 1:1 mixture of unlabeled acrylamide and deuterium-labeled acrylamide ([2,3,3'-D3]acrylamide), the proteins of interest were alkylated prior to electrophoretic separation. Copyright © 1992 Published by Elsevier Inc. https://doi.org/10.1016/0003-2697(92)90013-W. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Cysteine alkylation in unprotected peptides: synthesis of a carbavasopressin analog by intramolecular cysteine alkylation. This is Publication 111 from the Arizona State University Center for the Study of Early Events in Photosynthesis. Your Mendeley pairing has expired. Alkylation of cysteine in proteins with acrylamide under mildly alkaline conditions yields a thioether derivative, Cys-S-β-propionamide (Cys-S-Pam), which is stable during automated Edman degradation.Its phenylthiohydantoin derivative, PTH-Cys-S-Pam, is easily separated from other PTH-amino acids by HPLC and is thus useful for cysteine identification during protein sequencing. 8 publications. Yan Feng, Donald R. Menick, Bernice M. Katz, Charles J. Beischel, E. Starr Hazard, Saurav Misra, Thomas G. Ebrey, and Rosalie K. Crouch. Get article recommendations from ACS based on references in your Mendeley library. These metrics are regularly updated to reflect usage leading up to the last few days. An improved method for cysteine alkylation. Using a 1:1 mixture of unlabeled acrylamide and deuterium-labeled acrylamide ([2,3,3‘-D 3 ]acrylamide), the proteins of interest were alkylated prior to electrophoretic separation. Synthetic α-helical peptides incorporating intercalators for DNA recognition. Find more information on the Altmetric Attention Score and how the score is calculated.

Alkylation with iodoacetamide after cystine reduction results in the covalent addition of a carbamidomethyl group (57.07 Da) and prevents the formation of … Gemma Triola, Luc Brunsveld and Herbert Waldmann. Alkylation of cysteine-containing peptides J. Peptide Res. Methods are also presented for alkylation of cysteine in proteins adsorbed on fiberglass disks in the reaction cartridge of a protein sequencer. Alkylation of cysteine in proteins with acrylamide under mildly alkaline conditions yields a thioether derivative, Cys-S-β-propionamide (Cys-S-Pam), which is stable during automated Edman degradation. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Alkylation of cysteine with acrylamide for protein sequence analysis.

Racemization-Free Synthesis of S-Alkylated Cysteines via Thiol-ene Reaction. Alkylation with NEM is a measure of the reactivity and/or accessibility of a given Cys residue to this small, relatively hydrophobic, membrane-permeant thiol-specific reagent. You’ve supercharged your research process with ACS and Mendeley! Iodoacetamide is a sulfhydryl-reactive alkylating reagent used to block reduced cysteine residues for protein characterization and peptide mapping. 55, 2000 / 140–147 | 141. from those of the unreacted starting reagents, and thus the new compound was a candidate for 1.

We use cookies to help provide and enhance our service and tailor content and ads. Probing of the Retinal Binding Site of Bacteriorhodopsin by Affinity Labeling. Its phenylthiohydantoin derivative, PTH-Cys-S-Pam, is easily separated from other PTH-amino acids by HPLC and is thus useful for cysteine identification during protein sequencing. the Altmetric Attention Score and how the score is calculated. The Cysteine S-Alkylation Reaction as a Synthetic Method to Covalently Modify Peptide Sequences. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Cysteine Alkylation and SDS-PAGE. New ligands for boronate affinity chromatography. The work described here was partially supported by the Arizona State University Center for the Study of Early Events in Photosynthesis. Note: https://doi.org/10.1016/B978-008045382-8.00688-2, https://doi.org/10.1016/S0040-4039(01)00098-3, https://doi.org/10.1002/(SICI)1099-1352(199634/12)9:5/6<462::AID-JMR283>3.0.CO;2-G, https://doi.org/10.1016/0021-9673(94)00863-9.