TU Berlin

BiocatalysisPublications 2018 - 2019

Page Content

to Navigation

Publications

Painting argyrins blue: Negishi cross-coupling for synthesis of deep-blue tryptophan analogue β-(1-azulenyl)-l alanine and its incorporation into argyrin C
Citation key 177.2018.Stempel
Author Stempel, E. and Kaml, R. F. and Budisa, N. and Kalesse, M.
Year 2018
DOI 10.1016/j.bmc.2018.03.037
Journal Bioorg. Med. Chem.
Edition In press; epub ahead of print
Abstract The argyrins are a family of non-ribosomal peptides that exhibits different biological activities through only small structural changes. Ideally, a biologically active molecule can be tracked and observed in a variety of biological and clinical settings in a non-invasive manner. As a step towards this goal, we report here a chemical synthesis of unnatural deep blue amino acid β-(1-azulenyl)-l alanine with different fluorescence and photophysical properties, which allows a spectral separation from the native tryptophan signal. This might be especially useful for cell localization studies and visualizing the targeted proteins. In particular, the synthesis of β-(1-azulenyl)-l alanine was achieved through a Negishi coupling which proved to be a powerful tool for the synthesis of unnatural tryptophan analogs. Upon β-(1-azulenyl)-l alanine incorporation into argyrin C, deep blue octapeptide variant was spectrally and structurally characterized. Graphical abstract
Link to publication Link to original publication Download Bibtex entry

Navigation

Quick Access

Schnellnavigation zur Seite über Nummerneingabe