1218787-41-7Relevant academic research and scientific papers
Halomethyl-triazoles for rapid, site-selective protein modification
Brewster, Richard C.,Hulme, Alison N.
, (2021/09/20)
Post-translational modifications (PTMs) are used by organisms to control protein structure and function after protein translation, but their study is complicated and their roles are not often well understood as PTMs are difficult to introduce onto proteins selectively. Designing reagents that are both good mimics of PTMs, but also only modify select amino acid residues in proteins is challenging. Frequently, both a chemical warhead and linker are used, creating a product that is a misrepresentation of the natural modification. We have previously shown that biotin-chloromethyl-triazole is an effective reagent for cysteine modification to give S-Lys derivatives where the triazole is a good mimic of natural lysine acylation. Here, we demonstrate both how the reactivity of the alkylating reagents can be increased and how the range of triazole PTM mimics can be expanded. These new iodomethyl-triazole reagents are able to modify a cysteine residue on a histone protein with excellent selectivity in 30 min to give PTM mimics of acylated lysine side-chains. Studies on the more complicated, folded protein SCP-2L showed promising reactivity, but also suggested the halomethyl-triazoles are potent alkylators of methionine residues.
"click" synthesis of nonsymmetrical bis(1,2,3-triazoles)
Aizpurua, Jesus M.,Azcune, Itxaso,Fratila, Raluca M.,Balentova, Eva,Sagartzazu-Aizpurua, Malaien,Miranda, Jose I.
supporting information; experimental part, p. 1584 - 1587 (2010/06/16)
Chemical Fig. Repretation Unsymmetrically 1,1'-disubstituted 4,4'-bis-1 H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole Intermediates 5: (a) the stepwise Swern oxidatlon/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadiyne 9. The method is highlighted by Its compatibility with orthogonally protected and functlonallzed saccharide-peptide hybrids and its ability to be extended to the trlsubstituted counterparts 12.
