Abstract
trans-Cyclooctene groups incorporated into proteins via non-canonical amino acids (ncAAs) are emerging as specific handles for bioorthogonal chemistry. Here, we present a highly improved synthetic access to the axially and the equatorially linked trans-cyclooct-2-ene isomers (1a,b). We further show that the axially connected isomer has a half-life about 10 times higher than the equatorial isomer and reacts with tetrazines much faster, as determined by stopped-flow experiments. The improved properties resulted in different labeling performance of the insulin receptor on the surface of intact cells. Unnatural amino acids: A highly improved synthetic access to axially and equatorially linked trans-cyclooct-2-ene isomers is described. Furthermore, it was shown that the axially connected isomer has a half-life about 10 times higher than the equatorial isomer and reacts with tetrazines much faster, as determined by stopped-flow experiments (see figure).
Original language | English (US) |
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Pages (from-to) | 12266-12270 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 21 |
Issue number | 35 |
DOIs | |
State | Published - Aug 1 2015 |
Externally published | Yes |
Keywords
- amino acids
- cell labeling
- organic synthesis
- proteins
- receptors
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry