Nepsilon-thioacetyl-lysine: a multi-facet functional probe for enzymatic protein lysine Nepsilon-deacetylation
- PMID: 16697640
- DOI: 10.1016/j.bmcl.2006.04.075
Nepsilon-thioacetyl-lysine: a multi-facet functional probe for enzymatic protein lysine Nepsilon-deacetylation
Abstract
Peptides containing Nepsilon-thioacetyl-lysine and Nepsilon-acetyl-lysine were evaluated for their de(thio)acetylation catalyzed by human HDAC8 and SIRT1, two distinct protein deacetylases. Nepsilon-Thioacetyl-lysine was found to be a mimic of Nepsilon-acetyl-lysine for HDAC8-catalyzed reaction, but to confer inhibition against SIRT1. These results point to further diverse applications based on Nepsilon-thioacetyl-lysine.
Similar articles
-
N(epsilon)-methanesulfonyl-lysine as a non-hydrolyzable functional surrogate for N(epsilon)-acetyl-lysine.Org Biomol Chem. 2007 Mar 21;5(6):892-6. doi: 10.1039/b617185k. Epub 2007 Feb 5. Org Biomol Chem. 2007. PMID: 17340003
-
Mechanism-based inhibition of Sir2 deacetylases by thioacetyl-lysine peptide.Biochemistry. 2007 Dec 18;46(50):14478-86. doi: 10.1021/bi7013294. Epub 2007 Nov 21. Biochemistry. 2007. PMID: 18027980
-
Substrate specificity of SIRT1-catalyzed lysine Nepsilon-deacetylation reaction probed with the side chain modified Nepsilon-acetyl-lysine analogs.Bioorg Chem. 2010 Feb;38(1):17-25. doi: 10.1016/j.bioorg.2009.10.001. Epub 2009 Oct 24. Bioorg Chem. 2010. PMID: 19914676
-
Sirtuin mechanism and inhibition: explored with N(ε)-acetyl-lysine analogs.Mol Biosyst. 2011 Jan;7(1):16-28. doi: 10.1039/c0mb00033g. Epub 2010 Sep 15. Mol Biosyst. 2011. PMID: 20842312 Review.
-
NAD+-dependent deacetylation of H4 lysine 16 by class III HDACs.Oncogene. 2007 Aug 13;26(37):5505-20. doi: 10.1038/sj.onc.1210617. Oncogene. 2007. PMID: 17694090 Review.
Cited by
-
Multifunctional activity-based chemical probes for sirtuins.RSC Adv. 2023 Apr 14;13(17):11771-11781. doi: 10.1039/d3ra02133e. eCollection 2023 Apr 11. RSC Adv. 2023. PMID: 37063743 Free PMC article.
-
Substituting N(epsilon)-thioacetyl-lysine for N(epsilon)-acetyl-lysine in peptide substrates as a general approach to inhibiting human NAD(+)-dependent protein deacetylases.Int J Mol Sci. 2008 Jan;9(1):1-11. doi: 10.3390/ijms9010001. Epub 2008 Jan 7. Int J Mol Sci. 2008. PMID: 19325715 Free PMC article.
-
Sirtuin chemical mechanisms.Biochim Biophys Acta. 2010 Aug;1804(8):1591-603. doi: 10.1016/j.bbapap.2010.01.021. Epub 2010 Feb 2. Biochim Biophys Acta. 2010. PMID: 20132909 Free PMC article. Review.
-
Emerging Therapeutic Potential of SIRT6 Modulators.J Med Chem. 2021 Jul 22;64(14):9732-9758. doi: 10.1021/acs.jmedchem.1c00601. Epub 2021 Jul 2. J Med Chem. 2021. PMID: 34213345 Free PMC article. Review.
-
Novel thiourea-based sirtuin inhibitory warheads.Bioorg Med Chem Lett. 2015 Aug 15;25(16):3319-24. doi: 10.1016/j.bmcl.2015.05.058. Epub 2015 May 30. Bioorg Med Chem Lett. 2015. PMID: 26081291 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Chemical Information