Issue 12, 2013
From the journal:

Chemical Science

Scalable synthesis of γ-thiolysine starting from lysine and a side by side comparison with δ-thiolysine in non-enzymatic ubiquitination†

Remco Merkx,a   Gerjan de Bruin,a   Art Kruithof,a   Toine van den Bergh,b   Erwin Snip,b   Martin Lutz,c   Farid El Oualida  and  Huib Ovaa*a  

* Corresponding authors

a Division of Cell Biology, Netherlands Cancer Institute, Plesmanlaan 121, 1066 CX Amsterdam, The Netherlands
E-mail: h.ovaa@nki.nl

b Mercachem B.V., Kerkenbos 1013, 6546 BB Nijmegen, The Netherlands

c Bijvoet Centre for Biomolecular Research, Crystal and Structural Chemistry, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands

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.

Graphical abstract: Scalable synthesis of γ-thiolysine starting from lysine and a side by side comparison with δ-thiolysine in non-enzymatic ubiquitination

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Article information

DOI
https://doi.org/10.1039/C3SC51599K
Article type
Edge Article
Submitted
07 Jun 2013
Accepted
11 Sep 2013
First published
18 Sep 2013

Chem. Sci., 2013,4, 4494-4498

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Scalable synthesis of γ-thiolysine starting from lysine and a side by side comparison with δ-thiolysine in non-enzymatic ubiquitination

R. Merkx, G. de Bruin, A. Kruithof, T. van den Bergh, E. Snip, M. Lutz, F. El Oualid and H. Ovaa, Chem. Sci., 2013, 4, 4494 DOI: 10.1039/C3SC51599K

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