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Amino Acids for Diels–Alder Reactions in Living Cells
Author(s) -
Plass Tilman,
Milles Sigrid,
Koehler Christine,
Szymański Jędrzej,
Mueller Rainer,
Wießler Manfred,
Schultz Carsten,
Lemke Edward A.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201108231
Subject(s) - tetrazine , cycloaddition , norbornene , bioorthogonal chemistry , chemistry , azide , amino acid , click chemistry , combinatorial chemistry , organic chemistry , biochemistry , polymerization , catalysis , polymer
Under tension : A set of genetically encoded unnatural amino acids can be used for biocompatible site‐specific labeling of proteins with fluorogenic dyes. The new compounds have norbornene and trans ‐cyclooctene units that react with tetrazine derivatives in an inverse‐electron‐demand Diels–Alder cycloaddition (left in picture). The technique offers fast labeling that is orthogonal to labeling through azide–cyclooctyne click reaction (right).