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

Remco Merkx; G. de Bruin; Art Kruithof; T. van den Bergh; E. Snip; M. Lutz; F. El Oualid; H. Ovaa

doi:10.1039/C3SC51599K

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

Remco Merkx, G. de Bruin, Art Kruithof, T. van den Bergh, E. Snip, M. Lutz, F. El Oualid, H. Ovaa

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Abstract

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

Original language	English
Pages (from-to)	4494-4498
Number of pages	5
Journal	Chemical Science
Volume	4
Issue number	12
DOIs	https://doi.org/10.1039/C3SC51599K
Publication status	Published - 2013

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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 ubiquitination",

abstract = "We developed a scalable synthesis of g-thiolysine starting straight from lysine. The application of g-thiolysine was compared to d-thiolysine in the chemical synthesis of K48 and K33 linked diubiquitin conjugates. Both g- and d-thiolysine were found to perform equally efficiently as handles for nonenzymatic ubiquitination.",

author = "Remco Merkx and {de Bruin}, G. and Art Kruithof and {van den Bergh}, T. and E. Snip and M. Lutz and {El Oualid}, F. and H. Ovaa",

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doi = "10.1039/C3SC51599K",

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journal = "Chemical Science",

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AU - Merkx, Remco

AU - de Bruin, G.

AU - Kruithof, Art

AU - van den Bergh, T.

AU - Snip, E.

AU - Lutz, M.

AU - El Oualid, F.

AU - Ovaa, H.

PY - 2013

Y1 - 2013

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

U2 - 10.1039/C3SC51599K

DO - 10.1039/C3SC51599K

M3 - Article

SN - 2041-6520

VL - 4

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EP - 4498

JO - Chemical Science

JF - Chemical Science

IS - 12

ER -

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

Abstract

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