Environment-sensitive fluorescent tryptophan analogues <i>via</i> indole C-2 alkenylation reactions
A modular synthetic strategy for the preparation of intrinsically fluorescent unnatural α-amino acids by C-2 oxidation and alkenylation of a tryptophan-derived tetrahydro-β-carboline is described. This approach yielded a novel tryptophan-coumarin hybrid with strong environmental sensitivity and compatibility with near-infrared two-photon excitation.
Authors
- Andrew Sutherland (ORCID: https://orcid.org/0000-0001-7907-5766)
- Valeria K. Burianova (ORCID: https://orcid.org/0000-0002-5079-3374)
- Liyao Zeng (ORCID: https://orcid.org/0000-0001-5136-2042)
- Steven W. Magennis (ORCID: https://orcid.org/0000-0002-4327-8366)
- Alexander Thom
- Niamh C Radcliffe-Kennedy
Institutions
- University of Glasgow (GB)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc02114f
- Citations
- 4
- Primary Topic
- Alkaloids: synthesis and pharmacology
- Type
- article
- Field-Weighted Citation Impact
- 6.23