Amino acids for diels-alder reactions in living cells

Tilman Plass; Sigrid Milles; Christine Koehler; Jȩdrzej Szymański; Rainer Mueller; Manfred Wießler; Carsten Schultz; Edward A. Lemke

doi:10.1002/anie.201108231

Amino acids for diels-alder reactions in living cells

Tilman Plass, Sigrid Milles, Christine Koehler, Jȩdrzej Szymański, Rainer Mueller, Manfred Wießler, Carsten Schultz, Edward A. Lemke

Research output: Contribution to journal › Article › peer-review

264 Scopus citations

Abstract

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).

Original language	English (US)
Pages (from-to)	4166-4170
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	17
DOIs	https://doi.org/10.1002/anie.201108231
State	Published - Apr 23 2012
Externally published	Yes

Keywords

Diels-Alder reactions
amber suppression
click chemistry
protein engineering
unnatural amino acids

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201108231

Cite this

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abstract = "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).",

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AU - Plass, Tilman

AU - Milles, Sigrid

AU - Koehler, Christine

AU - Szymański, Jȩdrzej

AU - Mueller, Rainer

AU - Wießler, Manfred

AU - Schultz, Carsten

AU - Lemke, Edward A.

PY - 2012/4/23

Y1 - 2012/4/23

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AB - 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).

KW - Diels-Alder reactions

KW - amber suppression

KW - click chemistry

KW - protein engineering

KW - unnatural amino acids

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Amino acids for diels-alder reactions in living cells

Abstract

Keywords

ASJC Scopus subject areas

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