Development and biological applications of sulfur-triazole exchange (SuTEx) chemistry

被引:24
作者
Borne, Adam L. [1 ]
Brulet, Jeffrey W. [2 ]
Yuan, Kun [2 ]
Hsu, Ku-Lung [1 ,2 ,3 ,4 ]
机构
[1] Univ Virginia, Dept Pharmacol, Sch Med, Charlottesville, VA 22908 USA
[2] Univ Virginia, Dept Chem, McCormick Rd,POB 400319, Charlottesville, VA 22904 USA
[3] Univ Virginia, Univ Virginia Canc Ctr, Charlottesville, VA 22903 USA
[4] Univ Virginia, Dept Mol Physiol & Biol Phys, Charlottesville, VA 22908 USA
来源
RSC CHEMICAL BIOLOGY | 2021年 / 2卷 / 02期
基金
美国国家卫生研究院;
关键词
ACTIVITY-BASED PROBES; SERINE HYDROLASE ACTIVITIES; CLICK CHEMISTRY; DRUG DISCOVERY; PIPERIDYL-1,2,3-TRIAZOLE UREAS; NUCLEOPHILIC-SUBSTITUTION; SELECTIVE INHIBITORS; PROTEIN-DEGRADATION; EFFICIENT SYNTHESIS; SULFONYL FLUORIDES;
D O I
10.1039/d0cb00180e
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Sulfur electrophiles constitute an important class of covalent small molecules that have found widespread applications in synthetic chemistry and chemical biology. Various electrophilic scaffolds, including sulfonyl fluorides and arylfluorosulfates as recent examples, have been applied for protein bioconjugation to probe ligand sites amenable for chemical proteomics and drug discovery. In this review, we describe the development of sulfonyl-triazoles as a new class of electrophiles for sulfur-triazole exchange (SuTEx) chemistry. SuTEx achieves covalent reaction with protein sites through irreversible modification of a residue with an adduct group (AG) upon departure of a leaving group (LG). A principal differentiator of SuTEx from other chemotypes is the selection of a triazole heterocycle as the LG, which introduces additional capabilities for tuning the sulfur electrophile. We describe the opportunities afforded by modifications to the LG and AG alone or in tandem to facilitate nucleophilic substitution reactions at the SO2 center in cell lysates and live cells. As a result of these features, SuTEx serves as an efficient platform for developing chemical probes with tunable bioactivity to study novel nucleophilic sites on established and poorly annotated protein targets. Here, we highlight a suite of biological applications for the SuTEx electrophile and discuss future goals for this enabling covalent chemistry.
引用
收藏
页码:322 / 337
页数:16
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