Synthesis of Thiazoloindole α‑Amino Acids: Chromophores Amenable to One- and Two-Photon Induced Fluorescence

Dodds, A. C., Sansom, H. G., Magennis, S. W. and Sutherland, A. (2023) Synthesis of Thiazoloindole α‑Amino Acids: Chromophores Amenable to One- and Two-Photon Induced Fluorescence. Organic Letters, 25(49), pp. 8942-8946. (doi: 10.1021/acs.orglett.3c03851) (PMID:38055619) (PMCID:PMC10729019)

Abstract

Thiazoloindole α-amino acids have been synthesized in four steps from tryptophan using a dual-catalytic thiolation reaction and a copper-mediated intramolecular N-arylation process. Late-stage diversification of the thiazoloindole core with electron-deficient aryl substituents produced chromophores that on one-photon excitation displayed blue-green emission, mega-Stokes shifts, and high quantum yields. The thiazoloindole amino acids could also be excited via two-photon absorption in the near-infrared, demonstrating their potential for biomedical imaging applications.

• Item Type: Articles
• Additional Information: Financial support from the Carnegie Trust for the Universities of Scotland (Ph.D. studentship to A.C.D.), EPSRC (Ph.D. studentship to H.G.S., EP/T517896/1) and the University of Glasgow is gratefully acknowledged.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Magennis, Dr Steven and Sutherland, Professor Andrew and Dodds, Miss Amy and Sansom, Mr Henry
• Authors: Dodds, A. C., Sansom, H. G., Magennis, S. W., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Published Online: 06 December 2023
• Copyright Holders: Copyright © 2023 The Authors
• First Published: First published in Organic Letters 25(49):8942-8946
• Publisher Policy: Reproduced under a Creative Commons licence

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
312561		EPSRC DTP 2020/21	Christopher Pearce	Engineering and Physical Sciences Research Council (EPSRC)	EP/T517896/1	Research and Innovation Services