Ontology highlight
ABSTRACT:
SUBMITTER: Zhang Y
PROVIDER: S-EPMC5491101 | biostudies-literature | 2017 May
REPOSITORIES: biostudies-literature
Zhang Yingqian Y Zhou Xiaoping X Xie Yonghui Y Greenberg Marc M MM Xi Zhen Z Zhou Chuanzheng C
Journal of the American Chemical Society 20170420 17
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 alkali ...[more]