2012
DOI: 10.1002/anie.201106432
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Conversion of Cysteine into Dehydroalanine Enables Access to Synthetic Histones Bearing Diverse Post‐Translational Modifications

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Cited by 178 publications
(155 citation statements)
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“…Additionally, the disulfide attachment chemistry used has the attractive feature that the modification can be "erased" through simple reduction, thereby offering the potential to study, in a time-resolved way, the functional and structural consequences of PTM removal. Moreover, it may be possible to adapt the strategy to give nonreducible thioether linkages through use of alternate thiol-directed chemistries (36,37). Indeed, analogs of other PTMs can, in principle, be introduced chemically into preassembled chromatin using known cysteine derivatization routes-for example, lysine methylation (2) and acetylation (38).…”
Section: Discussionmentioning
confidence: 99%
“…Additionally, the disulfide attachment chemistry used has the attractive feature that the modification can be "erased" through simple reduction, thereby offering the potential to study, in a time-resolved way, the functional and structural consequences of PTM removal. Moreover, it may be possible to adapt the strategy to give nonreducible thioether linkages through use of alternate thiol-directed chemistries (36,37). Indeed, analogs of other PTMs can, in principle, be introduced chemically into preassembled chromatin using known cysteine derivatization routes-for example, lysine methylation (2) and acetylation (38).…”
Section: Discussionmentioning
confidence: 99%
“…This reaction has been used to install a number of thioether mimics of natural protein modifications such as lipidation, glycosylation, phosphorylation and lysine methylation/acetylation 164,165,167,168 , as well as installing reactive handles for further modification such as S-allyl cysteine for olefin metathesis. 131 These reactions typically (but not always) proceed with low substrate control in their diastereoselection and so a mixture of D/L-epimers is produced at the site of modification.…”
Section: Review Nature Communications | Doi: 101038/ncomms5740mentioning
confidence: 99%
“…6). Maleimides react rapidly, selectively, and irreversibly with thiolate-bearing residues such as the amino acid cysteine even in the presence of other nucleophiles such as lysine (39). We previously demonstrated that MLAmaleimide reacts covalently to ␣7 nAChR cysteine mutants in a time-dependent manner (32).…”
Section: Resultsmentioning
confidence: 99%