期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 47, 页码 16805-16811出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja104994d
关键词
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资金
- EPSRC
- Rhodes Trust
- National Science Foundation
- Royal Society
- Biotechnology and Biological Sciences Research Council [BB/C510824/1, BB/E004350/1, EGA17763] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/D023335/1, EP/E000614/1, GR/T26542/01, EP/G026688/1, EP/D023343/1] Funding Source: researchfish
- BBSRC [BB/E004350/1] Funding Source: UKRI
- EPSRC [EP/E000614/1, EP/G026688/1] Funding Source: UKRI
Olefin metathesis has recently emerged as a viable reaction for chemical protein modification. The scope and limitations of olefin metathesis in bioconjugation, however, remain unclear. Herein we report an assessment of various factors that contribute to productive cross-metathesis on protein substrates. Sterics, substrate scope, and linker selection are all considered. It was discovered during this investigation that allyl chalcogenides generally enhance the rate of alkene metathesis reactions. Ally; selenides were found to be exceptionally reactive olefin metathesis substrates, enabling a broad range of protein modifications not previously possible. The principles considered in this report are important not only for expanding the repertoire of bioconjugation but also for the application of olefin metathesis in general synthetic endeavors.
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