Article ; Online: Site-specific incorporation of quadricyclane into a protein and photocleavage of the quadricyclane ligation adduct.
Bioorganic & medicinal chemistry
2018 Volume 26, Issue 19, Page(s) 5280–5290
Abstract: The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative. Here we show that a QC amino acid can be incorporated into a protein site-specifically using the pyrrolysine-based genetic ...
Abstract | The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative. Here we show that a QC amino acid can be incorporated into a protein site-specifically using the pyrrolysine-based genetic code expansion platform, and subsequently used for ligation chemistry. Additionally, we exploited the photolability of the QC ligation product to render the adduct cleavable with a handheld UV lamp. We further developed a protein purification method that involves QC ligation of biotin to a protein of interest, capture on streptavidin resin, and finally release using only UV light. The QC ligation thus brings novel chemical manipulations to the realm of bioorthogonal chemistry. |
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MeSH term(s) | Biotin/chemistry ; Biotin/metabolism ; Bridged-Ring Compounds/chemistry ; Coordination Complexes/chemistry ; Lysine/analogs & derivatives ; Lysine/chemistry ; Nickel/chemistry ; Photolysis/radiation effects ; Streptavidin/chemistry ; Streptavidin/metabolism ; Ultraviolet Rays |
Chemical Substances | Bridged-Ring Compounds ; Coordination Complexes ; Biotin (6SO6U10H04) ; Nickel (7OV03QG267) ; quadricyclane (8E0K9BG24C) ; Streptavidin (9013-20-1) ; pyrrolysine (H3214Y96LP) ; Lysine (K3Z4F929H6) |
Language | English |
Publishing date | 2018-04-04 |
Publishing country | England |
Document type | Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S. |
ZDB-ID | 1161284-8 |
ISSN | 1464-3391 ; 0968-0896 |
ISSN (online) | 1464-3391 |
ISSN | 0968-0896 |
DOI | 10.1016/j.bmc.2018.04.009 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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