Highly Stable trans-Cyclooctene Amino Acids for Live-Cell Labeling

Jan Erik Hoffmann, Tilman Plass, Ivana Nikic, Iker Valle Aramburu, Christine Koehler, Hartmut Gillandt, Edward A. Lemke, Carsten Schultz

Research output: Contribution to journalArticle

28 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)12266-12270
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number35
DOIs
StatePublished - Aug 1 2015
Externally publishedYes

Fingerprint

Isomers
Labeling
Amino acids
Amino Acids
Insulin
Insulin Receptor
Experiments
Proteins

Keywords

  • amino acids
  • cell labeling
  • organic synthesis
  • proteins
  • receptors

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Hoffmann, J. E., Plass, T., Nikic, I., Aramburu, I. V., Koehler, C., Gillandt, H., ... Schultz, C. (2015). Highly Stable trans-Cyclooctene Amino Acids for Live-Cell Labeling. Chemistry - A European Journal, 21(35), 12266-12270. https://doi.org/10.1002/chem.201501647

Highly Stable trans-Cyclooctene Amino Acids for Live-Cell Labeling. / Hoffmann, Jan Erik; Plass, Tilman; Nikic, Ivana; Aramburu, Iker Valle; Koehler, Christine; Gillandt, Hartmut; Lemke, Edward A.; Schultz, Carsten.

In: Chemistry - A European Journal, Vol. 21, No. 35, 01.08.2015, p. 12266-12270.

Research output: Contribution to journalArticle

Hoffmann, JE, Plass, T, Nikic, I, Aramburu, IV, Koehler, C, Gillandt, H, Lemke, EA & Schultz, C 2015, 'Highly Stable trans-Cyclooctene Amino Acids for Live-Cell Labeling', Chemistry - A European Journal, vol. 21, no. 35, pp. 12266-12270. https://doi.org/10.1002/chem.201501647
Hoffmann JE, Plass T, Nikic I, Aramburu IV, Koehler C, Gillandt H et al. Highly Stable trans-Cyclooctene Amino Acids for Live-Cell Labeling. Chemistry - A European Journal. 2015 Aug 1;21(35):12266-12270. https://doi.org/10.1002/chem.201501647
Hoffmann, Jan Erik ; Plass, Tilman ; Nikic, Ivana ; Aramburu, Iker Valle ; Koehler, Christine ; Gillandt, Hartmut ; Lemke, Edward A. ; Schultz, Carsten. / Highly Stable trans-Cyclooctene Amino Acids for Live-Cell Labeling. In: Chemistry - A European Journal. 2015 ; Vol. 21, No. 35. pp. 12266-12270.
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