20443-80-5Relevant academic research and scientific papers
Liganding Functional Tyrosine Sites on Proteins Using Sulfur-Triazole Exchange Chemistry
Brulet, Jeffrey W.,Borne, Adam L.,Yuan, Kun,Libby, Adam H.,Hsu, Ku-Lung
supporting information, p. 8270 - 8280 (2020/05/25)
Tuning reactivity of sulfur electrophiles is key for advancing click chemistry and chemical probe discovery. To date, activation of the sulfur electrophile for protein modification has been ascribed principally to stabilization of a fluoride leaving group (LG) in covalent reactions of sulfonyl fluorides and arylfluorosulfates. We recently introduced sulfur-triazole exchange (SuTEx) chemistry to demonstrate the triazole as an effective LG for activating nucleophilic substitution reactions on tyrosine sites of proteins. Here, we probed tunability of SuTEx for fragment-based ligand discovery by modifying the adduct group (AG) and LG with functional groups of differing electron-donating and -withdrawing properties. We discovered the sulfur electrophile is highly sensitive to the position of modification (AG versus LG), which enabled both coarse and fine adjustments in solution and proteome activity. We applied these reactivity principles to identify a large fraction of tyrosine sites (～30%) on proteins (～44%) that can be liganded across >1500 probe-modified sites quantified by chemical proteomics. Our proteomic studies identified noncatalytic tyrosine and phosphotyrosine sites that can be liganded by SuTEx fragments with site specificity in lysates and live cells to disrupt protein function. Collectively, we describe SuTEx as a versatile covalent chemistry with broad applications for chemical proteomics and protein ligand discovery.
KINETICS OF THE SULFONYLATION OF SUBSTITUTED PHENOLS WITH BIPHENYLSULFONYL CHLORIDES IN THE PRESENCE OF TRIETHYLAMINE
Vizgert, R. V.,Maksimenko, N. N.,Budenkova, N. M.
, p. 509 - 513 (2007/10/02)
The kinetics of sulfonation by monosulfonyl chlorides YC6H4SO2Cl (Y = Ph, PhS, PhSO2) in substituted phenols XC6H4OH ( where X = H, p-CH3, p-OCH3, m-OH, m-CH3, p-Cl, p-Br ) in the presence of triethylamine in benzene were investigated in the range of 20-4
