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Highly Stable trans ‐Cyclooctene Amino Acids for Live‐Cell Labeling
Author(s) -
Hoffmann JanErik,
Plass Tilman,
Nikić Ivana,
Aramburu Iker Valle,
Koehler Christine,
Gillandt Hartmut,
Lemke Edward A.,
Schultz Carsten
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501647
Subject(s) - bioorthogonal chemistry , cyclooctene , chemistry , axial symmetry , amino acid , stereochemistry , combinatorial chemistry , biochemistry , click chemistry , catalysis , physics , quantum mechanics
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 ( 1 a , 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.