Fluorescent α-amino acids via Heck–Matsuda reactions of phenylalanine-derived arenediazonium salts

McGrory, R., Clarke, R. , Marshall, O. and Sutherland, A. (2023) Fluorescent α-amino acids via Heck–Matsuda reactions of phenylalanine-derived arenediazonium salts. Organic and Biomolecular Chemistry, 21(34), pp. 6932-6939. (doi: 10.1039/d3ob01096a) (PMID:37580965)

Abstract

The Heck–Matsuda coupling reaction of arenediazonium salts derived from L-phenylalanine with various alkenes has been developed. A two-step process involving the preparation of a tetrafluoroborate diazonium salt from a 4-aminophenylalanine derivative, followed by a palladium(0)-catalysed Heck–Matsuda coupling reaction allowed access to a range of unnatural α-amino acids with cinnamate, vinylsulfone and stilbene side-chains. Analysis of the photophysical properties of these unnatural α-amino acids demonstrated that the (E)-stilbene analogues exhibited fluorescent properties with red-shifted absorption and emission spectra and larger quantum yields than L-phenylalanine.

• Item Type: Articles
• Additional Information: Financial support from the University of Glasgow (Ph.D. studentship to RM) and the Engineering and Physical Sciences Research Council (EP/S029168/1) is gratefully acknowledged.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Marshall, Ms Olivia and Sutherland, Professor Andrew and McGrory, Miss Rochelle and Clarke, Ms Rebecca
• Authors: McGrory, R., Clarke, R., Marshall, O., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic and Biomolecular Chemistry
• Publisher: Royal Society of Chemistry
• ISSN: 1477-0520
• ISSN (Online): 1477-0539
• Published Online: 10 August 2023
• Copyright Holders: Copyright © The Royal Society of Chemistry 2023
• First Published: First published in Organic and Biomolecular Chemistry 21:6932-6939
• Publisher Policy: Reproduced under a Creative Commons licence

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
304762		Meta-Smart: Dynamic hybrid bio-plasmonic metamaterials.	Malcolm Kadodwala	Engineering and Physical Sciences Research Council (EPSRC)	EP/S029168/1	Chemistry