2019
DOI: 10.1002/open.201900224
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Light‐Driven Diselenide Metathesis in Peptides

Abstract: Peptides containing selenocysteine moieties are susceptible to non‐catalytic reactions of diselenide bonds metathesis induced by visible light. In contrast to previously reported radical metathesis of disulfide bridges in cysteine derivatives, this newly developed reaction is fast and clean, and proceeds without decomposition of peptides and without formation of side products. The diselenide bond in peptides was reported in literature to be more stable than the disulfide one and also less susceptible to metath… Show more

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Cited by 9 publications
(14 citation statements)
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“…55 ± 1.88 nm), which is consistent with previous reports [36,52]. The obvious D h difference observed between NCMs and CCMs may be attributed to the intramicellar covalent Se-Se network formation and concomitant shrinkage in the interface between the hydrophobic and hydrophilic portion of the mPEG-P(LA-DSeDEA)-PCL copolymer resulting in a more compact micellar structure [27,33,34]. Both NCMs and CCMs experienced suitable ζ-potentials for cellular attachment and internalization, −9.68 ± 3.03 and −13.1 ± 1.17, respectively.…”
Section: Self-assembly and Preparation Of Core Crosslinked Polymeric supporting
confidence: 90%
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“…55 ± 1.88 nm), which is consistent with previous reports [36,52]. The obvious D h difference observed between NCMs and CCMs may be attributed to the intramicellar covalent Se-Se network formation and concomitant shrinkage in the interface between the hydrophobic and hydrophilic portion of the mPEG-P(LA-DSeDEA)-PCL copolymer resulting in a more compact micellar structure [27,33,34]. Both NCMs and CCMs experienced suitable ζ-potentials for cellular attachment and internalization, −9.68 ± 3.03 and −13.1 ± 1.17, respectively.…”
Section: Self-assembly and Preparation Of Core Crosslinked Polymeric supporting
confidence: 90%
“…Se–Se bonds can also be cleaved by very mild redox signals such as H 2 O 2 and reduced GSH to form seleninic acid and selenol derivatives, respectively [ 62 ]. The observed redox stimuli-responsive propensity was primarily associated with the weak bond energy of the Se–Se bond at 172 kJ/mol [ 25 , 34 , 63 ]. This endowed diselenide containing polymers to be used in the fabrication of redox stimuli-responsive CCMs for the delivery and controlled release of CAs in tumor tissue.…”
Section: Resultsmentioning
confidence: 99%
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“…Visible light‐initiated generation of selenyl radicals with subsequent addition to terminal [32,33] or internal [34] alkynes has also been investigated. Significantly, catalyst‐free conditions can be used to realize both visible light‐induced metathesis reactions between diselenides and ditellurides [35] and diselenide metathesis between simple diorganyl diselenides [36] or Se−Se bond‐containing peptides [37] . Strikingly, there has been no profound study on selenocysteine (Sec)‐containing peptide modification under visible light conditions.…”
Section: Introductionmentioning
confidence: 99%