期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 17, 页码 6146-6151出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b00670
关键词
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资金
- NSFC [21572109, 21332004]
- Natural Science Foundation of Tianjin City [15JCYBJC53300]
- National Thousand Young Talents Program
- National Institute of General Medical Science [GM-063028]
5-Methylene pyrrolones (5MPs) are highly thiol-specific and tracelessly removable bioconjugation tools. 5MPs are readily prepared from primary amines in one step. 5MPs exhibit significantly improved stability under physiologically relevant conditions and cysteine specificity compared to commonly used analogues, maleimides. Michael addition of thiol to 5MPs occurs rapidly, cleanly, and does not generate a stereocenter. The conjugates efficiently release thiols via retro-Michael reaction in alkaline buffer (pH 9.5) or via thiol exchange at pH 7.5. This unique property makes 5MPs valuable for the controlled release of conjugated cargo and temporary thiol protection. The utilization of 5MPs for protein immobilization and pull-down of active complexes is illustrated using E. coli. acetohydroxyacid synthase isozyme I.
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