Synthesis and fluorescent properties of β-pyridyl α-amino acids

Harkiss, A. H., Bell, J. D., Knuhtsen, A., Jamieson, A. G. and Sutherland, A. (2019) Synthesis and fluorescent properties of β-pyridyl α-amino acids. Journal of Organic Chemistry, (doi:10.1021/acs.joc.9b00036) (Early Online Publication)

Harkiss, A. H., Bell, J. D., Knuhtsen, A., Jamieson, A. G. and Sutherland, A. (2019) Synthesis and fluorescent properties of β-pyridyl α-amino acids. Journal of Organic Chemistry, (doi:10.1021/acs.joc.9b00036) (Early Online Publication)

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Abstract

The preparation of a new class of β-pyridyl α-amino acid is described using a highly regioselective, ytterbium-catalyzed hetero Diels-Alder reaction of enones with vinyl ethers followed by a modified Knoevenagel-Stobbe reaction as the key heterocycle forming steps. Investigation of the properties and applications of these amino acids showed that they could be utilized in solid phase peptide synthesis for the preparation of a biologically relevant hexapeptide, while pyridines bearing electron-rich substituents exhibited strongly fluorescent properties with high quantum yields and MegaStokes shifts. A solvatochromic study with the most fluorogenic amino acid, a p-methoxyphenyl analogue revealed that this charge-transfer based chromophore is highly sensitive to solvent polarity with a bathochromic shift of 115 nm on changing from THF to phosphate-buffered saline.

Item Type:Articles
Status:Early Online Publication
Refereed:Yes
Glasgow Author(s) Enlighten ID:Knuhtsen, Dr Astrid and Harkiss, Mr Alexander and Bell, Mr Jonathan and Jamieson, Dr Andrew and Sutherland, Dr Andrew
Authors: Harkiss, A. H., Bell, J. D., Knuhtsen, A., Jamieson, A. G., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:06 February 2019
Copyright Holders:Copyright © 2019 American Chemical Society
First Published:First published in Journal of Organic Chemistry 2019
Publisher Policy:Reproduced in accordance with the publisher copyright policy

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
722351Sutherland ICASE 2015 (GSK)Andrew SutherlandEngineering and Physical Sciences Research Council (EPSRC)EP/N509176/1CHEM - CHEMISTRY