Scalable synthesis of γ-thiolysine starting from lysine and a side by side comparison with δ-thiolysine in non-enzymatic ubiquitinationElectronic supplementary information (ESI) available: Experimental procedures and characterization for all compounds, SDS PAGE analysis, HPLC-MS analysis, CD spectra, NMR spectra. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3sc51599k

We developed a scalable synthesis of γ-thiolysine starting straight from lysine. The application of γ-thiolysine was compared to δ-thiolysine in the chemical synthesis of K48 and K33 linked diubiquitin conjugates. Both γ- and δ-thiolysine were found to perform equally efficiently as handles for non-...

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Main Authors Merkx, Remco, de Bruin, Gerjan, Kruithof, Art, van den Bergh, Toine, Snip, Erwin, Lutz, Martin, El Oualid, Farid, Ovaa, Huib
Format Journal Article
LanguageEnglish
Published 28.10.2013
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Abstract We developed a scalable synthesis of γ-thiolysine starting straight from lysine. The application of γ-thiolysine was compared to δ-thiolysine in the chemical synthesis of K48 and K33 linked diubiquitin conjugates. Both γ- and δ-thiolysine were found to perform equally efficiently as handles for non-enzymatic ubiquitination. A scalable synthesis of γ-thiolysine and a side by side comparison to δ-thiolysine as a handle for non-enzymatic ubiquitination is reported.
AbstractList We developed a scalable synthesis of γ-thiolysine starting straight from lysine. The application of γ-thiolysine was compared to δ-thiolysine in the chemical synthesis of K48 and K33 linked diubiquitin conjugates. Both γ- and δ-thiolysine were found to perform equally efficiently as handles for non-enzymatic ubiquitination. A scalable synthesis of γ-thiolysine and a side by side comparison to δ-thiolysine as a handle for non-enzymatic ubiquitination is reported.
Author Snip, Erwin
El Oualid, Farid
Kruithof, Art
van den Bergh, Toine
Lutz, Martin
Merkx, Remco
de Bruin, Gerjan
Ovaa, Huib
AuthorAffiliation Crystal and Structural Chemistry
Division of Cell Biology
Bijvoet Centre for Biomolecular Research
Mercachem B.V
Netherlands Cancer Institute
Utrecht University
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Electronic supplementary information (ESI) available: Experimental procedures and characterization for all compounds, SDS PAGE analysis, HPLC-MS analysis, CD spectra, NMR spectra. For ESI and crystallographic data in CIF or other electronic format see DOI
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Snippet We developed a scalable synthesis of γ-thiolysine starting straight from lysine. The application of γ-thiolysine was compared to δ-thiolysine in the chemical...
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Title Scalable synthesis of γ-thiolysine starting from lysine and a side by side comparison with δ-thiolysine in non-enzymatic ubiquitinationElectronic supplementary information (ESI) available: Experimental procedures and characterization for all compounds, SDS PAGE analysis, HPLC-MS analysis, CD spectra, NMR spectra. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3sc51599k
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