期刊
ORGANIC LETTERS
卷 22, 期 8, 页码 2920-2924出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00578
关键词
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资金
- National Key Research and Development Program of China [2017YFA0505200]
- National Natural Science Foundation of China [21625201, 21661140001, 91853202, 21521003, 21702182, 21873081]
- Bei j i n g Outstanding Young Scien t i s t Program [BJJWZYJH01201910001001]
- China Postdoctoral Science Foundation [2018M640546]
- Fundamental Research Funds for the Central Universities [2019QNA3009]
We report here a deep mechanistic study of the click ortho-quinone methide (oQM) cycloaddition between ortho-quinolinone quinone methide (oQQM) and thio-vinyl ether (TV), named as TQ-ligation. DFT calculations revealed the unexpected fact that dehydration of oQQM precursors is the rate-determining step of this transformation, and two highly reactive oQQM precursors were predicted. Guided by the calculations, a new click oQM cycloaddition which shows significantly improved kinetics and remarkable efficiency on protein labeling was developed.
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