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- W2029837691 abstract "Reversible lysine acetylation and methylation regulate the function of a wide variety of proteins, including histones. Here, we have synthesized azalysine-containing peptides in acetylated and unacetylated forms as chemical probes of the histone deacetylases (HDAC8, Sir2Tm, and SIRT1) and the histone demethylase, LSD1. We have shown that the acetyl-azalysine modification is a fairly efficient substrate for the sirtuins, but a weaker substrate for HDAC8, a classical HDAC. In addition to deacetylation by sirtuins, the acetyl-azalysine analogue generates a novel ADP-ribose adduct that was characterized by mass spectrometry, Western blot analysis, and nuclear magnetic resonance spectroscopy. This peptide-ADP-ribose adduct is proposed to correspond to a derailed reaction intermediate, providing unique evidence for the direct 2′-hydroxyl attack on the O-alkylimidate intermediate that is formed in the course of sirtuin catalyzed deacetylation. An unacetylated azalysine-containing H3 peptide proved to be a potent inhibitor of the LSD1 demethylase, forming an FAD adduct characteristic of previously reported related structures, providing a new chemical probe for mechanistic analysis." @default.
- W2029837691 created "2016-06-24" @default.
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- W2029837691 date "2012-03-12" @default.
- W2029837691 modified "2023-10-17" @default.
- W2029837691 title "Azalysine Analogues as Probes for Protein Lysine Deacetylation and Demethylation" @default.
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- W2029837691 doi "https://doi.org/10.1021/ja209574z" @default.
- W2029837691 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3313494" @default.
- W2029837691 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/22352831" @default.
- W2029837691 hasPublicationYear "2012" @default.
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